Fragrance Systems for Scented Consumer Products

Abstract

The present invention relates to a fragrance system and a perfumed consumer product comprising the fragrance system, as well as a method and use of the fragrance system for enhancing, imparting, improving and / or modifying the odor characteristics and / or odor intensity of the perfumed consumer product, comprising core-shell microcapsules A, optionally core-shell microcapsules B, and optionally free perfume oil, wherein the core of the core-shell microcapsules A and / or the free perfume oil comprises a 2-oxoacetate derivative of formula (I).

Description

[Technical Field]

[0001] The present invention relates to a fragrance system and a perfumed consumer product comprising the fragrance system, as well as a method and use of the fragrance system for enhancing, imparting, improving and / or modifying the odor characteristics and / or odor intensity of the perfumed consumer product, comprising core-shell microcapsules A, optionally core-shell microcapsules B, and optionally free perfume oil, wherein the core of the core-shell microcapsules A and / or the free perfume oil comprises a 2-oxoacetate derivative of formula (I).

[0002] Background of the Invention One of the problems facing the fragrance industry is that the olfactory benefits provided by fragrance compounds are lost relatively quickly due to volatility, especially the volatility of "top notes."In addition, some fragrance components may be unstable in functional fragrance applications and may be lost due to decomposition or rapid evaporation.These problems are often addressed through the use of delivery systems, such as capsules containing fragrance, to release fragrance in a controlled manner.Although fragrance encapsulation can at least partially solve the evaporation problem, many types of microcapsules are known to lose part of their fragrance during storage due to diffusion through their shells or walls, or due to the nature of consumer products that contain surfactants that can leak fragrance.To minimize fragrance leakage, the cross-linking of capsule walls can be increased.However, in order to perceive the fragrance containing such systems, it is necessary to either mechanically break the microcapsules or allow the fragrance to spontaneously leak from the capsules for a desired period of time. In the first case, the olfactory experience is limited to the scratching episode, while in the second case, performance issues are usually encountered due to issues related to the limited shelf life of consumer products containing microcapsules.

[0003] It is therefore desirable to create new perfume systems that are able to solve or at least reduce the above-mentioned problems.

[0004] It is also desirable to improve the performance of, for example, light-induced scent release of the perfume system and light-induced expansion or cleavage of the capsule wall.

[0005] It would also be desirable to provide manufacturing rules for fragrance systems that allow for improved performance of such systems.

[0006] The present invention provides a solution that overcomes the above-mentioned drawbacks associated with known fragrance compositions, in particular for improving the performance of fragrance systems. [Brief explanation of the drawings]

[0007] [Figure 1] FIG. 1 shows the dynamic headspace concentration of 2-phenylacetaldehyde produced from 2-phenylethyl 2-oxo-2-phenylacetate (O1) of formula (I) upon light irradiation of various fragrance systems containing various amounts of perfume raw materials of group B in microcapsules A or B or in free perfume oil (see Example 5). [Figure 2] FIG. 1 shows the dynamic headspace concentration of 2-phenylacetaldehyde produced from 2-phenylethyl 2-oxo-2-phenylacetate (O1) of formula (I) upon light irradiation of fragrance systems containing various amounts of perfume raw materials of group B in microcapsules A (see Example 6).

[0008] Detailed Description of the Invention In a first aspect, the present invention provides a method for producing a medicament for the treatment of a pulmonary arthritis, comprising: a) core-shell microcapsules A, b) optionally, core-shell microcapsules B; c) optionally, perfume oil in free form; Including, The core of the core-shell microcapsules A and / or the perfume oil in free state, if present, may be of formula (I) [ka] [In the formula, R 1 is a straight or branched C1-C alkyl group optionally containing 1 to 4 oxygen atoms that are not directly attached to a carbonyl group; 22 represents an alkyl or alkenyl group, or a cyclic C3-C8 alkyl or alkenyl group optionally containing 1 to 4 oxygen atoms that are not directly bonded to a carbonyl group, or a phenyl group optionally substituted by a C1-C4 alkyl group; R 2 is a straight, branched or cyclic C1-C optionally containing 1 to 4 oxygen atoms 22 represents a hydrocarbon group, R 3 represents a hydrogen atom or a C1-C optionally containing 1-2 oxygen atoms 10 represents a hydrocarbon group, or R 2 and R 3 Together, C 5~16 Cycloalkyl groups, C 5~16 Cycloalkenyl group, C 4~14 Heterocycloalkyl group or C 4~14 forming a heterocycloalkenyl group] including the 2-oxoacetate derivative of Related to aromatics.

[0009] For purposes of clarity, the term "optionally" means that any ingredient may or may not be included in the fragrance system.

[0010] For the sake of clarity, the expression "fragrance system" means that the perfuming composition is designed to provide an olfactory impression to the consumer by using a scent delivery system, such as microcapsules or core-shell microcapsules. In certain embodiments, the fragrance system is designed to provide the consumer with long-lasting and / or high-performance fragrance.

[0011] For the sake of clarity, expressions like "core-shell microcapsules" are meant to denote capsules having a particle size distribution in the micron range (e.g., a mean diameter (d(v,0.5)) comprised between about 1 and 3000 μm) and comprising an outer solid oligomeric or polymeric shell and an inner continuous phase which is an oil phase (i.e., a hydrophobic material) encapsulated by the outer shell. For the avoidance of doubt, coacervates are also considered to be core-shell microcapsules in the present invention.

[0012] According to one embodiment, the microcapsules have a mean diameter comprised between 1 and 500 microns, preferably between 2 and 200 microns, and more preferably between 4 and 100 microns.

[0013] Core-shell microcapsules A and B can be of the same shell type or of different shell types. The nature of the shell of the microcapsules can be varied.

[0014] The material encapsulating the hydrophobic material composition can be a microcapsule, which has been widely described in the prior art.

[0015] According to certain embodiments, the shell comprises a material selected from the group consisting of polyurea, polyurethane, polyamide, polyester, poly(meth)acrylate (i.e., polyacrylate and / or polymethacrylate), polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, polymers of melamine and formaldehyde, polymers of melamine and urea, or polymers of melamine and glyoxal, and mixtures thereof. The shell can also be a hybrid shell, i.e., an organic-inorganic shell, for example, a hybrid shell composed of at least two types of crosslinked inorganic particles or a shell obtained by the hydrolysis and condensation reaction of a polyalkoxysilane macromonomer composition.

[0016] According to certain embodiments, the core-shell microcapsules may also be obtained by using different or more than one encapsulation method.

[0017] In a preferred embodiment, the shells of microcapsules A and B may each independently be selected from the group of aminoplast, polyamide, polyester, polyurea and polyurethane shells and mixtures thereof.

[0018] In certain embodiments, the shell of microcapsules A and / or B comprises an aminoplast copolymer, such as melamine-formaldehyde or urea-formaldehyde or crosslinked melamine formaldehyde or melamine glioxal.

[0019] In certain embodiments, the shells of microcapsules A and / or B are polyurea-based, for example, but not limited to, prepared from an isocyanate-based monomer and an amine-containing crosslinker, such as guanidine carbonate and / or guanazole. Certain polyurea microcapsules comprise a polyurea wall that is the reaction product of the polymerization of at least one polyisocyanate containing at least two isocyanate functional groups with at least one reactant selected from the group consisting of an amine (e.g., a water-soluble guanidine salt and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated fragrance. However, the use of the amine can be omitted.

[0020] In certain embodiments, the colloidal stabilizer comprises an aqueous solution of 0.1% to 0.4% polyvinyl alcohol, 0.6% to 1% cationic copolymer of vinylpyrrolidone and quaternized vinylimidazole (all percentages defined by weight relative to the total weight of the colloidal stabilizer). In certain embodiments, the emulsifier is an anionic or amphiphilic biopolymer, which may be selected from the group consisting of gum arabic, soy protein, gelatin, sodium caseinate, and mixtures thereof.

[0021] In certain embodiments, the shell of microcapsules A and / or B is polyurethane-based, such as, but not limited to, prepared from polyisocyanates and polyols, polyamides, polyesters, and the like.

[0022] In certain embodiments, microcapsules A and / or B have a polymer shell obtained by complex coacervation, in which case this shell is possibly crosslinked.

[0023] In certain embodiments of core-shell microcapsules, core-shell microcapsules A and / or B comprise an oil-based core comprising a hydrophobic active agent, preferably a fragrance, and a composite shell comprising a first material and a second material, where the first material is a coacervate and the second material is a polymeric material, and the first and second materials are different.

[0024] In a particular embodiment, the weight ratio between the first material and the second material is comprised between 50:50 and 99.9:0.1.

[0025] In certain embodiments, the coacervate comprises a first polyelectrolyte, preferably selected from among proteins (e.g., gelatin), polypeptides or polysaccharides (e.g., chitosan), most preferably gelatin, and a second polyelectrolyte, preferably alginate, cellulose derivatives guar gum, pectinate, carrageenan, polyacrylic and methacrylic acid or xanthan gum, or even a vegetable gum, such as acacia gum (gum arabic), most preferably gum arabic.

[0026] The first material of the coacervate can be hardened chemically using a suitable cross-linking agent, such as glutaraldehyde, glyoxal, formaldehyde, tannic acid, or genipin, or can be hardened enzymatically using an enzyme, such as transglutaminase.

[0027] The second polymeric material may be selected from the group consisting of polyurea, polyurethane, polyamide, polyester, polyacrylate, polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, polymers of melamine and formaldehyde, polymers of melamine and urea or polymers of melamine and glyoxal and mixtures thereof, preferably polyurea and / or polyurethane. The second material is preferably present in an amount of less than 3 wt. %, preferably less than 1 wt. %, based on the total weight of the microcapsule slurry.

[0028] The preparation of aqueous dispersions / slurries of core-shell microcapsules is well known to those skilled in the art. In certain embodiments, the microcapsule wall material may comprise any suitable resin, particularly melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc. Suitable resins include the reaction products of aldehydes and amines, and suitable aldehydes include formaldehyde and glyoxal. Suitable amines include melamine, urea, benzoguanamine, glycoluril, and mixtures thereof. Suitable melamines include methylolmelamine, methylated methylolmelamine, iminomelamine, and mixtures thereof. Suitable ureas include dimethylolurea, methylated dimethylolurea, urea-resorcinol, and mixtures thereof. Materials suitable for production can be obtained from one or more of the following companies: Solutia Inc. (St. Louis, Missouri, USA), Cytec Industries (West Paterson, New Jersey, USA), and Sigma-Aldrich (St. Louis, Missouri, USA).

[0029] In certain embodiments of core-shell microcapsules, core-shell microcapsules A and / or B are - an oil-based core containing a hydrophobic active substance, preferably a fragrance; - optionally an inner shell prepared from polymerized multifunctional monomers; - a protein-containing biopolymer shell, in which at least one protein is cross-linked; Includes.

[0030] According to a particular embodiment, the protein is selected from the group consisting of milk proteins, caseinates such as sodium or calcium caseinate, casein, whey proteins, hydrolyzed proteins, gelatin, gluten, pea proteins, soy proteins, silk proteins and mixtures thereof, preferably sodium caseinate, most preferably sodium caseinate.

[0031] According to a particular embodiment, the protein comprises sodium caseinate and globular proteins, preferably selected from the group consisting of whey protein, beta-lactoglobulin, ovalbumin, bovine serum albumin, vegetable proteins and mixtures thereof.

[0032] The protein is preferably a mixture of sodium caseinate and whey protein.

[0033] According to certain embodiments, the biopolymer shell comprises cross-linked proteins selected from the group consisting of sodium caseinate and / or whey protein.

[0034] According to a particular embodiment, the core-shell microcapsules A and / or B are - an oil-based core containing a hydrophobic active substance, preferably a fragrance; - an inner shell prepared from polymerized polyfunctional monomers, preferably polyisocyanates having at least two isocyanate functional groups; - a biopolymer shell comprising a protein, in which at least one protein is cross-linked, preferably a mixture comprising sodium caseinate and a globular protein, preferably whey protein; - optionally at least an outer mineral layer Includes.

[0035] According to one embodiment, the sodium caseinate and / or whey protein are cross-linked proteins.

[0036] The weight ratio of sodium caseinate to whey protein is preferably 0.01-100, preferably 0.1-10, and more preferably 0.2-5.

[0037] In certain embodiments, microcapsules A and / or B comprise: 1) mixing perfume oil with at least one polyisocyanate having at least two isocyanate functional groups to form an oil phase; 2) dispersing or dissolving an aminoplast resin and, optionally, a stabilizer in water to form an aqueous phase; 3) preparing an oil-in-water dispersion having an average droplet size comprised between 1 and 100 microns by mixing an oil phase and an aqueous phase; 4) carrying out a curing step to form the walls of the microcapsules; and 5) Optionally, drying the final dispersion to obtain dried core-shell microcapsules. and one-shell aminoplast core-shell microcapsules obtainable by a method comprising:

[0038] In certain embodiments, the core-shell microcapsules A and / or B are formaldehyde-free capsules. A typical method for producing an aminoplast-formaldehyde-free microcapsule slurry is as follows: 1) preparing an oligomer composition comprising a reaction product of the following a to c or obtained by reacting a to c: a. a polyamine component in the form of melamine or a mixture of melamine with at least one C1-C4 compound containing two NH2 functional groups; b. Glyoxal and C 4-6 a mixture of 2,2-dialkoxy-ethanal and, optionally, glyoxalate (the mixture being glyoxal / C in a ratio of 1 / 1 to 10 / 1); 4-6 an aldehyde component in the form of an aldehyde component having a molar ratio of 2,2-dialkoxy-ethanal; c. Protonic acid catalyst; 2) preparing an oil-in-water dispersion having a droplet size comprised between 1 and 600 microns, wherein said oil-in-water dispersion is a. Oil, b. aqueous medium; c. at least one oligomeric composition obtained in step 1; d. Below: i. C4~C 12Aromatic or aliphatic diisocyanates or triisocyanates and their biurets, triuret, trimers, trimethylolpropane adducts and mixtures thereof; and / or ii. Formula: Q-(oxiran-2-ylmethyl) n [wherein n represents 2 or 3, and Q represents 2 to 6 nitrogen atoms and / or acid atoms] represents a C2-C6 group optionally containing a nitrogen atom] Dioxirane or trioxirane compounds of at least one cross-linking agent selected from e. Optionally, a C1-C4 compound containing two NH2 functional groups Contains; 3) heating the dispersion; and 4) cooling the dispersion Includes.

[0039] The above method is described in more detail in WO 2013 / 068255.

[0040] In certain embodiments, the core-shell microcapsules A and / or B are an oil-based core containing a hydrophobic active substance, preferably a fragrance; - below: Acyl chlorides, a first amino compound, and Second amino compound a polyamide shell comprising or obtainable from Includes.

[0041] According to a particular embodiment, the core-shell microcapsules A and / or B comprise an oil-based core containing a hydrophobic active substance, preferably a fragrance, and one of the following: acyl chlorides, advantageously in an amount comprised between 5 and 98% w / w, preferably between 20 and 98% w / w, more preferably between 30 and 85% w / w; a first amino compound, advantageously in an amount comprised between 1% and 50% w / w, preferably between 7 and 40% w / w; a second amino compound, advantageously in an amount comprised between 1% and 50% w / w, preferably between 2 and 25% w / w; a stabilizer, preferably a biopolymer, advantageously in an amount comprised between 0 and 90%, preferably between 0.1 and 75%, more preferably between 1 and 70% and a polyamide shell comprising or obtainable from Includes.

[0042] According to a particular embodiment, the core-shell microcapsules A and / or B are an oil-based core containing a hydrophobic active substance, preferably a fragrance; - below: Acyl chlorides, a first amino compound, preferably an amino acid selected from the group consisting of L-lysine, L-arginine, L-histidine, L-tryptophan and / or mixtures thereof; a second amino compound selected from the group consisting of ethylenediamine, diethylenetriamine, cystamine and / or mixtures thereof; and a biopolymer selected from the group consisting of casein, sodium caseinate, bovine serum albumin, whey protein, and / or mixtures thereof; wherein the first amino compound may be different from the second amino compound.

[0043] Typically, the method for producing polyamide-based microcapsules A and / or B comprises the following steps: a) dissolving at least one acyl chloride in a hydrophobic material, preferably a fragrance, to form an oil phase; b) dispersing the oil phase obtained in step a) into an aqueous phase containing a first amino compound to form an oil-in-water emulsion; c) carrying out a curing step to form polyamide microcapsules in the form of a slurry; A stabilizer is added to the oil phase and / or the water phase, At least one second amino compound is added to the aqueous phase before the formation of the oil-in-water emulsion and / or to the oil-in-water emulsion obtained after step b).

[0044] In certain embodiments, the shell of microcapsules A and / or B is polyurea-based or polyurethane-based. Examples of methods for producing polyurea-based and polyurethane-based microcapsule slurries are described, for example, in WO 2007 / 004166, EP 2300146 and EP 2579976. Typically, the method for producing polyurea-based or polyurethane-based microcapsule slurries comprises the following steps: a) dissolving at least one polyisocyanate having at least two isocyanate groups in oil to form an oil phase; b) preparing an aqueous solution of an emulsifier or colloidal stabilizer to form an aqueous phase; c) adding the oil phase to the water phase to form an oil-in-water dispersion with an average droplet size comprised between 1 and 500 μm, preferably between 5 and 50 μm; and d) applying conditions sufficient to induce interfacial polymerization to form microcapsules in the form of a slurry. Includes.

[0045] In certain embodiments, microcapsules A and / or B can be in the form of a powder, and can be obtained in particular by subjecting the microcapsule slurry to a drying process, such as spray drying, to provide the microcapsules as such, i.e., in the form of a powder. It is understood that any standard method known to those skilled in the art for carrying out such drying can be applied. In particular, the slurry can be spray-dried, preferably in the presence of a polymeric carrier material, such as polyvinyl acetate, polyvinyl alcohol, dextrin, natural or modified starch, gum arabic, vegetable gum, pectin, xanthan, alginate, carrageenan, or a cellulose derivative, to provide the microcapsules in the form of a powder.

[0046] However, other drying methods that meet certain criteria, such as those disclosed in WO 2017 / 134179, such as extrusion, plating, spray granulation, fluidized bed methods or drying at room temperature using further materials (carriers, desiccants), may also be mentioned.

[0047] The core of the core-shell microcapsules A and / or B is in the form of an oil phase. The term "oil phase" of the core or "core oil phase" means a liquid or solution at 20°C and 1 atm pressure that is capable of providing a benefit or effect to its surrounding environment, and in particular comprises a perfume, flavoring, cosmetic, skin care, malodor control, bactericide, fungicide, pharmaceutical or pesticide ingredient, diagnostic agent and / or insect repellent or attractant.

[0048] The oil phase can be composed of a single compound or a mixture of compounds, at least one of which has at least one property that makes it useful as a fragrance, flavoring, cosmetic, skin care, malodor control, bactericide, fungicide, pharmaceutical or pesticide ingredient, diagnostic agent, and / or insect repellent or attractant.

[0049] Preferably, the oil phase may be composed of a single compound or a mixture of compounds, at least one of which has at least one property that makes it useful as a fragrance, flavoring, cosmetic, skin care, malodor control, bactericide, fungicide, pharmaceutical or pesticide ingredient and / or insect repellent or attractant.

[0050] Indeed, the invention is practiced in exactly the same way regardless of the exact nature of the oil phase. Thus, although the invention will be further described herein below with specific reference to "perfuming" ingredients, it will be understood that the following embodiments are applicable to other oils as well (i.e., the term "perfuming agent" can be replaced with, for example, "flavoring," "cosmetic," "skin care," "malodor control," "bactericide," "fungicide," "medicine," "pesticide," "diagnostic agent," "insect attractant," or "insect repellent").

[0051] In a preferred embodiment, the oil phase comprises a fragrance, optionally a solvent, optionally a fragrance co-ingredient, and optionally a fragrance adjuvant.

[0052] The term "fragrance" is understood to mean a single perfuming ingredient or a mixture of ingredients in the form of a perfuming composition.

[0053] The term "perfuming ingredient" or "perfuming co-ingredient" is understood herein to mean a compound used as an active ingredient in a perfume preparation or composition to provide a pleasant effect when applied to a surface. That is, to be considered a perfuming compound, such a compound must be recognized by those skilled in the art of perfumery as being capable of imparting or modifying the odor of a composition, article, or surface in a positive or pleasant way, rather than simply having an odor. Furthermore, this definition is also meant to include compounds that do not necessarily have an odor, but are capable of adjusting the odor of a perfumed composition, perfumed article, or surface, and thus modifying the odor perception of such a composition, article, or surface by the user.

[0054] The nature and type of perfuming co-ingredients present in the base do not warrant a more detailed description herein, and in any case, would not be comprehensive; those skilled in the art can select them based on their general knowledge, according to the intended use or application and the desired sensory effect. Generally, perfuming ingredients belong to various chemical classes, such as hydrocarbons, alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, thiols, terpenoids, nitrogenous or sulfurous heterocyclic compounds, and essential oils, and said perfuming ingredients can be of natural or synthetic origin. Specific examples of such perfuming ingredients can be found in current literature, such as *Perfume and Flavor Chemicals* by S. Arctander, Montclair, NJ (USA), 1969 (and later revised editions) or other works of a similar nature, as well as in the vast number of patents and other literature related to the fragrance industry. They are well known to those skilled in the art of perfuming consumer products, i.e., imparting pleasant odors to consumer products.

[0055] By "solvent" is meant a material that is substantially neutral from the perfumery point of view, i.e., does not significantly alter the sensory properties of the perfuming ingredients, and is generally not miscible with water, i.e., has a solubility in water of less than 10% or even less than 5%. Solvents commonly used in perfumery, such as dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate, limonene or other terpenes, isoparaffins, such as those known under the trademark Isopar® (supplier: Exxon Chemical), or glycol ethers and glycol ether esters, such as those known under the trademark Dowanol® (supplier: Dow Chemical Company), are suitable solvents for the purposes of the present invention.

[0056] "Perfume adjuvant" means an ingredient capable of imparting additional benefits, such as color, chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in perfume bases cannot be exhaustive, but it must be mentioned that said ingredients are well known to those skilled in the art.

[0057] The 2-oxoacetate derivatives of formula (I) can be used inside core-shell microcapsules, for example as part of the oil phase, particularly inside core-shell microcapsule A, to generate gas upon exposure to light, thereby expanding or destroying the capsule wall. Furthermore, the 2-oxoacetates of formula (I) can be used as pre-fragrances inside core-shell microcapsules and / or in free fragrances to generate, in addition to gas, a perfumed aldehyde or ketone upon exposure to light.

[0058] Preferably, R 1 represents a linear or branched C1-C4 alkyl or alkenyl group, or a cyclic C3-C7 alkyl or alkenyl group, or a phenyl group optionally substituted with a C1-C4 alkyl group. More preferably, R 1 represents a methyl group, a cyclopentyl group, a cyclohexyl group or a phenyl group. Most preferably, R 1 represents a phenyl group.

[0059] Preferably, R 2 is a straight, branched or cyclic C4-C optionally containing 1 to 4 oxygen atoms 20 represents a hydrocarbon group.

[0060] Preferably, R 3 represents a hydrogen atom or a C1-C optionally containing 1-2 oxygen atoms 10 represents any of the hydrocarbon groups.

[0061] Preferably, R 2 and R 3 Together, C5~16 Cycloalkyl groups, C 5~16 Cycloalkenyl group, C 4~14 Heterocycloalkyl group or C 4~14 It forms a heterocycloalkenyl group.

[0062] More preferably, OCH(R 2 )(R 3 ) group has the formula O=CH(R 2 ) (i.e., R 3 (is H) 20 Perfume aldehydes or the corresponding C6-C of the formula O=C(R2)(R3) 20 It is obtained from fragrance ketones.

[0063] Even more preferably, OCH(R 2 )(R 3 ) group has the formula O=CH(R 2 ) corresponding C6~C 12 It is derived from perfume aldehydes.

[0064] Most preferably, the formula O=CH(R 2 ) the fragrance aldehyde is selected from the group consisting of benzaldehyde, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2,6-dimethyl-5-heptenal (melonal), 3,7-dimethyl-2,6-octadienal (citral), 3,7-dimethyl-6-octenal (citronellal), decanal, 4-dodecenal, 3-hexenal, 7-hydroxy-3,7-dimethyloctanal, 2-methylundecanal and 2-phenylacetaldehyde.

[0065] Most preferably, the formula O=C(R 2 )(R 3 ) perfume ketones are selected from the group consisting of oct-2-en-4-one and 2-isopropyl-5-methylcyclohexan-1-one.

[0066] In certain embodiments, the 2-oxoacetate derivative of formula (I) is 3-(4-tert-butyl-1-cyclohexen-1-yl)propyl 2-oxo-2-phenylacetate, 3-(4-tert-butylphenyl)-2-methylpropyl 2-cyclohexyl-2-oxoacetate, 3-(4-(tert-butyl)phenyl)-2-methylpropyl 2-oxo-2-phenylacetate, decyl 2-cyclohexyl-2-oxoacetate, decyl 2-oxo-2-phenylacetate, (2,4-dimethyl-3-cyclohexene-1-yl)propyl 2-oxo-2-phenylacetate, -yl)methyl 2-cyclohexyl-2-oxoacetate, (2,4-dimethyl-3-cyclohexen-1-yl)methyl 2-oxo-2-phenylacetate, 1-(3,3- and 5,5-dimethyl-1-cyclohexen-1-yl)-4-pentenyl 2-oxo-2-phenylacetate, 3-(3,3- and 1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)propyl 2-oxo-2-phenylacetate, 2,6-dimethyl-5-heptenyl 2-oxo-2-phenylacetate, 3,7-dimethyl-2,6-oxo-2-phenylacetate octadienyl 2-cyclohexyl-2-oxoacetate, 3,7-dimethyl-2,6-octadienyl 2-(4-methylcyclohexyl)-2-oxoacetate, 3,7-dimethyl-2,6-octadienyl 3-methyl-2-oxopentanoate, 3,7-dimethyl-2,6-octadienyl 2-oxo-2-phenylacetate, 3,7-dimethyl-2,6-octadienyl 2-oxopropanoate, 3,7-dimethyl-6-octenyl 2-(4-acetylphenyl)-2-oxoacetate, 3,7-dimethyl-6-octenyl ( bicyclo[2.2.1]hept-2-exo-yl)oxoacetate, 3,7-dimethyl-6-octenyl 2-cyclohexyl-2-oxoacetate, 3,7-dimethyl-6-octenyl 2-cyclopentyl-2-oxoacetate, 3,7-dimethyl-6-octenyl 2-(4-methylcyclohexyl)-2-oxoacetate, 3,7-dimethyl-6-octenyl[4-(2-methyl-1,3-dioxolan-2-yl)phenyl]oxoacetate, 3,7-dimethyl-6-octenyl 3-methyl-2-oxopentadecanoate, 3,7-Dimethyl-6-octenyl 3-methyl-2-oxopentanoate, 3,7-dimethyl-6-octenyl 2-oxobutanoate, 3,7-dimethyl-6-octenyl 2-oxohexadecanoate, 3,7-dimethyl-6-octenyl 2-oxopentanoate, 3,7-dimethyl-6-octenyl 2-oxo-2-phenylacetate, 3,7-dimethyl-6-octenyl 2-oxopropanoate, 4-(1,1-dimethylpropyl)cyclohexyl cyclohexyl 2-cyclohexyl-2-oxoacetate, 4-dodecenyl 2-oxo-2-phenylacetate, (3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl 2-oxo-2-phenylacetate, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethyl 2-oxo-2-phenylacetate, 3-hexenyl 2-oxo-2-phenylacetate phenyl acetate, 3-hexenyl 2-oxopropanoate, 7-hydroxy-3,7-dimethyloctyl 2-oxo-2-phenylacetate, [4- and 3-(4-hydroxy-4-methylpentyl)-3-cyclohexen-1-yl]methyl 2-oxo-2-phenylacetate, 2-isopropyl-5-methylcyclohexyl 2-cyclohexyl-2-oxoacetate, 2-isopropyl-5-methylcyclohexyl 2-oxo-2-phenylacetate phenyl acetate, 4-methoxybenzyl 2-cyclohexyl-2-oxoacetate, [4- and 3-(4-methyl-3-pentenyl)-3-cyclohexen-1-yl]methyl 2-oxo-2-phenylacetate, 3-methyl-5-phenylpentyl 2-oxo-2-phenylacetate, 2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-pentenyl 2-oxo-2-phenylacetate, 2,6-Nonadienyl 2-oxo-2-phenylacetate, 3-nonenyl 2-oxo-2-phenylacetate, oct-2-en-4-yl 2-oxo-2-phenylacetate, 2-pentylcyclopentyl 2-cyclohexyl-2-oxoacetate, 4-phenylbutan-2-yl 2-oxo-2-phenylacetate, 2-phenylethyl 2-oxo-2-phenylacetate, 2-phenylethyl 2-oxopropanoate, 3,5,6,6-tetramethyl-4-methylenehepta undecenyl 2-oxo-2-phenylacetate, 4-(2,6,6-trimethyl-2-cyclohexenyl)-3-buten-2-yl 2-oxo-2-phenylacetate, benzyl 2-oxo-2-phenylacetate, 2-hexyl 2-oxo-2-phenylacetate, 2-methylundecyl 2-oxo-2-phenylacetate, 9-undecenyl 2-oxo-2-phenylacetate or 10-undecenyl 2-oxo-2-phenylacetate. In particular, the 2-oxoacetate derivatives of formula (I) are 2-phenylethyl 2-oxo-2-phenylacetate, 3-hexyl 2-oxo-2-phenylacetate, benzyl 2-oxo-2-phenylacetate, (2,4-dimethyl-3-cyclohexen-1-yl)methyl 2-oxo-2-phenylacetate, 3,7-dimethyl-2,6-octadienyl 2-oxo-2-phenylacetate, 3,7-dimethyl-6-octenyl 2-oxo-2-phenylacetate, 7-hydroxybenzoyl ... The 2-oxo-2-phenylacetate may be 3,7-dimethyloctyl 2-oxo-2-phenylacetate, decyl 2-oxo-2-phenylacetate, 4-dodecenyl 2-oxo-2-phenylacetate, 2-isopropyl-5-methylcyclohexyl 2-oxo-2-phenylacetate, 2-methylundecyl 2-oxo-2-phenylacetate, oct-2-en-4-yl 2-oxo-2-phenylacetate, or 2,6-dimethyl-5-heptenyl 2-oxo-2-phenylacetate.

[0067] "Hydrocarbon group" means that the group consists of hydrogen and carbon atoms and can be in the form of an aliphatic hydrocarbon, i.e., a straight-chain or branched-chain saturated hydrocarbon (e.g., an alkyl group), a straight-chain or branched-chain unsaturated hydrocarbon (e.g., an alkenyl or alkynyl group), a saturated cyclic hydrocarbon (e.g., a cycloalkyl group), or an unsaturated cyclic hydrocarbon (e.g., a cycloalkenyl or cycloalkynyl group), or an aromatic hydrocarbon, i.e., an aryl group, or a mixture of the above types of groups; for example, a specific group can contain straight-chain alkyl, branched-chain alkenyl (e.g., having one or more carbon-carbon double bonds), (poly)cycloalkyl, and aryl moieties, unless a specific limitation to only one type is mentioned. Similarly, in all embodiments of the present invention, when a group is referred to as being in the form of more than one type of topology (e.g., straight-chain, cyclic, or branched) and / or as being saturated or unsaturated (e.g., alkyl, aromatic, or alkenyl), it is understood to also mean a group that can have any one of the above topologies or contain moieties that are saturated or unsaturated, as explained above. Similarly, in all embodiments of the present invention, when a group is referred to as being in one type of saturated or unsaturated form (e.g., alkyl), it means that the group can be in any type of topology (e.g., linear, cyclic, or branched) or can have multiple moieties with different topologies.

[0068] For the sake of clarity, expressions such as "optionally comprising", "optionally containing" or "optionally substituted" mean that the group to which reference is made may comprise, contain or be substituted by, for example, the following functional groups or groups: alcohol groups, ketone groups, aldehyde groups, ether groups, ester groups and / or carboxylic acid groups.

[0069] The 2-oxoacetate derivatives of formula (I) are either encapsulated in core-shell microcapsules A or used in free perfume oil, or a combination thereof. According to the present invention, the 2-oxoacetate derivatives of formula (I) in the core-shell microcapsules A and / or in the free perfume oil can be one single structure according to formula (I) or a mixture of different structures according to formula (I).

[0070] In a particular embodiment, the fragrance system comprises core-shell microcapsule A and free perfume oil. In another particular embodiment, the fragrance system comprises core-shell microcapsule A and core-shell microcapsule B.

[0071] In certain embodiments, the fragrance system comprises core-shell microcapsules A, core-shell microcapsules B, and free perfume oil.

[0072] The fragrance system according to the present invention comprises core-shell microcapsules A.

[0073] In a particular embodiment, the aromatic core-shell microcapsules A are at least one 2-oxoacetate derivative of formula (I), - optionally at least one perfume raw material of Group A, - maximum 20% by weight of Group B flavouring ingredients and optionally, a solvent Includes.

[0074] In a preferred embodiment, the core-shell microcapsules A comprise at least one 2-oxoacetate derivative of formula (I).

[0075] Thus, preferably, the core-shell microcapsules A comprise at least one 2-oxoacetate of formula (I), optionally one or more perfume raw materials of group A, up to 20% by weight of one or more perfume raw materials of group B, and optionally a solvent.

[0076] Preferably, the amount of 2-oxoacetate derivative of formula (I) in the core-shell microcapsule A is at least 25% by weight (based on the total weight of the microcapsule A), more preferably at least 50% by weight, more preferably at least 80% by weight, and most preferably at least 90% by weight.

[0077] Core-shell microcapsules A containing almost exclusively one or more 2-oxoacetate derivatives of formula (I) have the particular advantage that they more easily generate a gas overpressure inside the capsule, thereby more easily expanding or cleaving the capsule wall to release the photochemically generated fragrance raw material.

[0078] If the fragrance is encapsulated, the 2-oxoacetate derivative of formula (I) is preferably in a separate capsule.

[0079] The perfume raw materials of group A do not interfere (or only to a minimal extent) with the light-induced decomposition of the 2-oxoacetate derivatives of formula (I).The perfume raw materials of group A can be used in the fragrance systems according to the invention in amounts that are independent of the amount of the 2-oxoacetate derivatives of formula (I).

[0080] The term "interferes with the light-induced decomposition of 2-oxoacetate" means that the presence of these ingredients has a negative effect on the rate of light-induced decomposition of 2-oxoacetate compared to their absence. This means that the presence of these compounds slows or even prevents the decomposition of 2-oxoacetate. There are several ways in which fragrance ingredients can interfere with the decomposition of 2-oxoacetate, such as by strongly absorbing UVA radiation or by quenching one of the intermediate (excited) states of the photoreaction.

[0081] The fragrance raw materials were prepared by dissolving the fragrance raw materials and 2-oxoacetate (1.5 g L ) in a 1:1 weight ratio in non-degassed acetonitrile. -1) at 3.1mWcm -2 A sample is considered to be in Group A if 50% or less of ethyl 2-oxo-2-phenylacetate (used as the reference compound) remains after 40 minutes of UVA radiation at 25°C.

[0082] The perfume raw materials of Group A in the fragrance system of the present invention are allyl 2-(cyclohexyloxy)acetate, allyl 3-cyclohexylpropanoate, allyl heptanoate, allyl hexanoate, benzaldehyde, benzyl acetate, benzyl benzoate, benzyl 2-hydroxybenzoate, 2-cyclohexylethyl acetate, cyclohexyl 2-hydroxybenzoate, 4-cyclohexyl-2-methyl-2-butanol, decanal, diethyl 1,4-cyclohexanedicarboxylate, (2,2-dimethoxy) methyl ... (dimethyl)benzene, 6,6-dimethoxy-2,5,5-trimethyl-2-hexene, 2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl acetate, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 2,6-dimethyl-2-heptanol, 2,6-dimethyl-5-heptanal, 6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane, 3,7-dimethyl-2,6- and 3,6 -Nonadienenitrile, 3,7-dimethyl-1,6-nonadien-3-ol, 3,7-dimethyl-2,6-octadienal, (E)-3,7-dimethyl-2,6-octadienol, (Z)-3,7-dimethyl-2,6-octadienol, 3,7-dimethyl-1,6-octadien-3-ol, 3,7-dimethyl-2,6-octadienyl acetate, 3,7-dimethyl-3-octanol, 3,7-dimethyl-6-octenenitrile, 3,7-dimethyl-6-octen-1-ol, 2,6-dimethyl-7-octene-2 -ol, 3,7-dimethyl-6-octenyl acetate, 1,1-dimethyl-2-phenylethyl butanoate, 1,1-dimethyl-2-phenylethyl acetate, 3,3-dimethyl-5-[2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 1,4-dioxacycloheptadecane-5,17-dione, dodecanal, dodecanol, (Z)-4-dodecenal, ethyl butanoate, ethyl 3-hydroxybut-2-enoate, ethyl 2-methylbutanoate, ethyl 2-methyl-1,3-Dioxolane-2-acetate, ethyl 2-methylpentanoate, ethyl 3-oxobutanoate, 3-(2- and 4-ethylphenyl)-2,2-dimethylpropanal, (2E)-2-ethyl-4-[2,2,3-trimethyl-3-cyclopenten-1-yl]-2-buten-1-ol, 6-ethyl-2,10,10-trimethyl-1-oxaspiro[4.5]deca-3,6-diene, 5-heptyldihydro-2(3H)-furanone, 4,6 ,6,7,8,8-Hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethanone, (Z)-3-hexen-1-ol, (Z)-3-hexenyl acetate, (Z)-3-hexenyl 2-hydroxybenzoate, hexyl acetate, 5-hexyldihydrofuran-2(3H)-one, hexyl 2-hydroxybenzoate benzoate, hexyl 2-methylpropanoate, 3- and 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 1-isopropyl-4-methylbenzene, 2-isopropyl-5-methylcyclohexan-1-ol, isopropyl 2-methylbutanoate, 4-isopropyl-1-methylcyclohexyl acetate, 3-(3-isopropyl-1-phenyl)butanal, 3-(4-isopropylphenyl)-2 -methylpropanal, isopropyl tetradecanoate, 4-methoxybenzaldehyde, 1-methoxy-4-methylbenzene, 3-(4-methoxyphenyl)-2-methylpropanal, 4-(2-methoxy-2-propanyl)-1-methylcyclohexene, 1-methoxy-4-(2-propenyl)benzene, 6-methoxy-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulene, methyl benzoate, 7-methyl-2H-1,5-Benzodioxepin-3(4H)-one, 3-methyl-2-buten-1-yl acetate, 2- and 3-methylbutyl acetate, 2- and 3-methylbutyl butyrate, 2-methylbutyl 2-hydroxybenzoate, 2-(4-methylcyclohex-3-enyl)propan-2-ol, 2-(4-methyl-3-cyclohexen-1-yl)-2-propanyl acetate, 2-{2-[4-methyl-3-cyclohexen-1-yl]propyl}cyclopentanone, (E)-4-methyl-3-decen-5-ol, methyl 2,2-di Methyl-6-methylidenecyclohexanecarboxylate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 5-methylheptan-3-one oxime, methyl 7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylate and methyl 7-isopropyl-1,4a-dimethyltetradecahydrophenanthrene-1-carboxylate, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde , 2-methyl-3-[4-(2-methyl-2-propanyl)phenyl]propanal, 4-methyl-2-(2-methyl-1-propen-1-yl)tetrahydro-2H-pyran, methyl 2-octinoate, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 4-methyl-4-penten-2-yl 2-methylpropanoate, 3-methyl-5-phenyl-1-pentanol, 5-methyl-2-(2-propanyl)cyclohexanone, 1-methyl-4-(2-propanyl)-1,4-cyclohexadiene, 4-(2-methyl- 2-propanyl)cyclohexanol, 2-(2-methyl-2-propanyl)cyclohexyl acetate, 4-(2-methyl-2-propanyl)cyclohexyl acetate, 1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene, 2-methyl-4-propyl-1,3-oxathiane, (3E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohex-1-yl)-3-buten-2-one, methyl 2,6,6-trimethyl-3-cyclohexene-1-carboxylate, (3E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one and (1E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol, 2-methylundecanal, 2,6-nonadienal, 2,6-nonadienol, nonanal, octanal, oct-2-en-4-one, oxacyclohexadecan-2-one, 1-oxa-12- and 13-cyclohexadecen-2-one, 1,1'-oxacyclohexadecan ... Dibenzoylbenzene, pentyl 2-hydroxybenzoate, 2-phenoxyethanol, 2-phenylacetaldehyde, 3-phenylbutanal, 2-phenylethanol, 2-phenylethyl acetate, phenylmethanol, 4-[(2-propanyl)cyclohexyl]methanol, 7-propyl-2H-benzo[b][1,4]dioxepin-3(4H)-one, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 1-(3,6,8,8-tetramethylisobutyl)-2H-benzo[b][1,4]dioxepin-3(4H)-one 1-(2,3,8,8-tetramethyl-1,2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulen-5-yl)ethan-1-one, 2,3,6,7- and 2,4,6,8-tetramethylnonan-1-ol, 3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-yl acetate, 2,2,6,8-tetramethyl-1,2,3,4,4a,5,8,8a-octahydro-1-naphthalenol, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-, 1,2,3,5,6,7,8,8a- and 1,2,3,4,6,7 ,8,8a-octahydronaphthalen-2-yl)ethan-1-one, tricyclo[5.2.1.0(2,6)]dec-3- and 4-en-8-yl acetate, 2,2,2-trichloro-1-phenylethyl acetate, tricyclo[5.2.1.0(2,6)]dec-3- or 4-en-8-yl propanoate, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate, 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, 2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-1-cyclohexanol, 2-, 3- and 4-(5,5,6-trimethylbicyclo[2.2.1]hept-2-yl)-1-cyclohexanol, (2E)-1-[2,6,6-trimethyl-1-cyclohexen-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-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-(2,6,6 -trimethyl-3-cyclohexen-1-yl)-2-buten-1-one, 3,8,9-, 4,6,8- and 4,7,9-trimethyldecan-2-ol, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2,2,5-trimethyl-5-pentylcyclopentanone, 2,6,6-trimethylspiro[bicyclo[3.1.1]heptane-3,1'-cyclohexane]-2'-en-4'-one, undecanal, 1,3,5-undecatriene and 10-undecenal.

[0083] The amount of Group A perfume raw materials in core-shell microcapsule A may be present in an amount greater than 30 wt.%, greater than 50 wt.%, greater than 70 wt.%, or greater than 90 wt.% (based on the total weight of microcapsule A). In particular, the amount of Group A perfume raw materials in core-shell microcapsule A may be present in an amount of up to 70 wt.%, preferably up to 60 wt.%, preferably up to 50 wt.%, preferably up to 40 wt.%, preferably up to 30 wt.%, preferably up to 20 wt.%, preferably up to 10 wt.%, more preferably up to 50 wt.%.

[0084] The perfume raw materials of Group B inhibit the light-induced decomposition of the 2-oxoacetate derivatives of Formula (I). Such materials interact with the 2-oxoacetate derivatives of Formula (I), for example, slowing down the photoreactions that cause performance degradation. Surprisingly, the perfume raw materials of Group B can inhibit the light-induced decomposition of the 2-oxoacetate even if they are physically separated from the 2-oxoacetate, for example, by encapsulating them in a separate capsule (microcapsule B) or by having them in the free perfume oil, while the 2-oxoacetate is encapsulated, for example, in microcapsule A. The perfume raw materials of Group B should be encapsulated in a minimum amount in core-shell microcapsules A or B, regardless of whether the 2-oxoacetate is encapsulated in the same or different core-shell microcapsules or whether the 2-oxoacetate is part of the free perfume oil. Additionally, Group B perfume raw materials should also be used in minimal amounts in the free perfume oil, whether the 2-oxoacetate is encapsulated or part of the free oil.

[0085] The fragrance raw materials were prepared by dissolving the fragrance raw materials and 2-oxoacetate (1.5 g L ) in a 1:1 weight ratio in non-degassed acetonitrile. -1 ) at 3.1mWcm -2 After irradiation with UVA radiation at 25°C for 40 minutes, if more than 50% of ethyl 2-oxo-2-phenylacetate (used as the reference compound) remains, it is considered to be in Group B.

[0086] The Group B perfume raw materials in the fragrance system of the present invention are benzo[d][1,3]dioxole-5-carbaldehyde, (E)-1-(benzyloxy)-2-methoxy-(4-prop-1-en-1-yl)benzene, 2H-chromen-2-one, 1,2-dimethoxy-4-[(1E)-1-propen-1-yl]benzene, 1,5-dimethyl-1-vinyl-4-hexenyl(E)-3-phenylpropenoate, (E)-2-hexyl-3-phenyl-2-propenal, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, 2-isobutylquinoline, 2-methoxynaphthalene, 2-methoxy-4-(2-propen-1-yl)phenol, 2-methoxy-4-[(1E)-1-propen-1-yl]phenol, 2-methyl ... and (3E)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one.

[0087] When Group B perfume ingredients are encapsulated, they are more efficiently retained and therefore prevent photoreactions from occurring for longer, and therefore, most preferably, photoreactions are avoided or the Group B perfume ingredients will be used in minimal amounts.

[0088] Thus, aromatic core-shell microcapsules A comprise up to 10 wt. % of Group B perfume raw materials (based on the total weight of microcapsules A); more preferably, up to 5 wt. % of Group B perfume raw materials, and most preferably, aromatic core-shell microcapsules A contain no Group B perfume raw materials.

[0089] The fragrance system according to the invention may further comprise optional core-shell microcapsules B.

[0090] In a particular embodiment, the aromatic core-shell microcapsules B are - at least one fragrance raw material of Group A, - maximum 30% by weight of Group B flavouring ingredients and optionally, a solvent Includes.

[0091] The amount of Group A perfume raw materials in core-shell microcapsules B is preferably at least 70% by weight (based on the total weight of microcapsules B), more preferably at least 80% by weight, and most preferably at least 90% by weight.

[0092] The amount of Group B perfume raw materials is preferably less than 30% by weight (based on the total weight of microcapsule B), more preferably less than 20% by weight, even more preferably less than 10% by weight, and most preferably core-shell microcapsule B does not contain any Group B perfume raw materials.

[0093] The fragrance system according to the invention optionally further comprises a free perfume oil. For the sake of clarity, "free perfume oil" means a perfume oil as defined above, for example, not encapsulated or part of a core-shell microcapsule A or B.

[0094] In certain embodiments, the aromatic free perfume oil comprises: - at least one fragrance raw material of Group A, - optionally at least one perfume raw material of Group B, optionally at least one 2-oxoacetate derivative of formula (I) and optionally, a solvent Includes.

[0095] The amount of Group A perfume raw materials in the free fragrance is preferably at least 70% by weight (based on the total weight of the free fragrance), more preferably at least 80% by weight, and most preferably at least 90% by weight.

[0096] Preferably, the free perfume oil comprises no more than 50% by weight (based on the total weight of the free fragrance), preferably less than 30% by weight, more preferably less than 20% by weight, even more preferably less than 10% by weight of Group B perfume raw materials.

[0097] Most preferably, the free perfume oil does not contain any Group B perfume raw materials.

[0098] In a particular embodiment, the aromatic free perfume oil contains 0.1 to 20% by weight of the 2-oxoacetate derivative of formula (I). More preferably, the aromatic free perfume oil contains 1 to 10% by weight of the 2-oxoacetate derivative of formula (I), most preferably 2 to 5% by weight of the 2-oxoacetate derivative of formula (I).

[0099] In certain embodiments, the aromatic free perfume oil comprises a 2-oxoacetate derivative of formula (I), and core-shell microcapsules A and, optionally, core-shell microcapsules B do not comprise perfume raw materials of group B.

[0100] In certain embodiments, aromatic core-shell microcapsules A and core-shell microcapsules B do not contain any Group B perfume raw materials.

[0101] More preferably, core-shell microcapsule A comprises the 2-oxoacetate derivative of formula (I) and core-shell microcapsule B comprises at least one perfume material of group A, optionally when the perfume oil in free state also does not comprise any perfume raw materials of group B.

[0102] Preferably, the Group B perfume raw materials are part of the free perfume oil. Most preferably, the Group B perfume raw materials are not used in the presence of the 2-oxoacetate of formula (I).

[0103] In certain embodiments, the aromatic system comprises: a. core-shell microcapsules A, the core of which comprises, or preferably consists of, a 2-oxoacetate derivative of formula (I) and optionally a solvent; b. core-shell microcapsules B, the core of which comprises a perfume ingredient of Group A; and c. Perfume oil in the free state, optionally containing up to 20% of perfume raw materials of group B, or additionally containing no perfume raw materials of group B, and / or containing 2-oxoacetate derivatives of formula (I) and / or perfume raw materials of group A. Includes.

[0104] In a further aspect, the present invention provides a method for producing a composition comprising: i) Aromatic systems as defined above; ii) at least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and iii) optionally at least one flavor adjuvant The present invention relates to a perfume composition comprising:

[0105] The term "perfume carrier" is understood to mean a material that is substantially neutral from a perfumery point of view, i.e., that does not significantly alter the sensory properties of the perfuming ingredients. In some embodiments, the carrier can be a liquid.

[0106] As liquid carrier, as non-limiting example, can be mentioned emulsifying system, that is, solvent and surfactant system, or solvent that is commonly used in perfumery.It is not possible to cover the detailed description of the nature and type of solvent that is commonly used in perfumery.However, as non-limiting example, can be mentioned the most commonly used solvents, for example, ethanol, water, dipropylene glycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol or ethyl citrate.

[0107] The term "perfume base" is understood to be a composition comprising at least one perfuming co-ingredient.

[0108] The term "perfuming co-ingredient" has the same meaning as defined above.

[0109] The term "fragrance adjuvant" has the same meaning as defined above.

[0110] The compositions of the present invention, which comprise the fragrance system of the present invention and at least one perfume carrier, and the perfumed compositions, which comprise the fragrance system of the present invention, at least one perfume carrier, at least one perfume base and, optionally, at least one perfume adjuvant, represent particular embodiments of the present invention.

[0111] In a further aspect, the present invention provides a method for producing a composition comprising: i) as perfuming ingredient, at least an aromatic system as defined above; and ii) Consumer product base relating to consumer products, including

[0112] Such consumer products can be solid or liquid products. According to certain embodiments, liquid products are preferred. For the purpose of clarity, "consumer product" refers to a consumer product that is typically perfumed and is expected to provide at least a perfume effect, i.e., a perfumed consumer product.

[0113] For the sake of clarity, "consumer product base" herein refers to a base formulation that is compatible with the perfuming ingredients according to the present invention, in particular the fragrance microcapsules, comprising the photolabile 2-oxoacetate of formula (I), and is expected to impart a pleasant odor to the surface to which it is applied (e.g., skin, hair, fabrics, or hard surfaces). That is, a perfumed consumer product according to the present invention comprises an unperfumed base functional formulation corresponding to a desired consumer product, such as a detergent, fabric softener, or air freshener, and an olfactory-effective amount of the microcapsules according to the present invention. Of course, such consumer products can also contain non-encapsulated fragrances, i.e., fragrance ingredients in free form.

[0114] The nature and type of ingredients of consumer product bases do not justify a more detailed description herein, which would in any case not be exhaustive, and the skilled person is able to select them on the basis of his general knowledge and according to the nature and desired effect of the product.

[0115] In certain embodiments, the perfumed consumer product comprises a fragrance, a fabric care product, a body care product, an air care product, or a home care product.

[0116] In certain embodiments, the perfumed consumer product is a fine perfume, a liquid or solid fabric detergent, a fabric softener, a fabric refresher, an ironing water, a shampoo, a coloring formulation, a hairspray, a deodorant or antiperspirant, a perfumed soap, a shower or bath mousse, an oil or gel, a hygiene product, an air freshener, a "ready to use" powder air freshener, or a hard surface cleaner. Most preferably, the perfumed consumer product is a liquid or solid fabric detergent, a fabric softener, a fabric refresher, an ironing water, an air freshener, a "ready to use" powder air freshener, or a hard surface cleaner.

[0117] The proportions at which the fragrance system of the present invention can be incorporated into the various aforementioned consumer products vary within a wide range of values. These values ​​depend on the nature of the article to be perfumed and the desired sensory effect, as well as the nature of the auxiliary ingredients in a given consumer product base. Typically, consumer products contain from about 0.01% by weight to about 80% by weight of the fragrance system of the present invention, based on the total weight of the consumer product.

[0118] Preferably, the consumer product comprises from about 0.01% to about 30% of the fragrance system, more preferably from about 0.1% to about 15% of the fragrance system.

[0119] In a further aspect, the present invention relates to the use of a perfume system to enhance, impart, improve and / or modify the scent profile and / or scent intensity of a perfumed consumer product.

[0120] The definitions of fragrance system and consumer product are the same as those mentioned above.

[0121] The present invention also relates to a method for enhancing, imparting, improving and / or modifying the scent profile and / or scent intensity by applying the above-defined fragrance system to a perfumed consumer product.

[0122] The definitions of perfume system and consumer product are the same as those defined above.

[0123] In a further aspect, the present invention relates to the use of an aromatic system for enhancing or prolonging the diffusion effect of the characteristic scent of a fragrance ingredient on a surface, characterized in that said surface is treated, preferentially in the presence of light, with an aromatic system as defined above or a perfumed consumer product as defined above under conditions that allow the release of at least an aldehyde and / or ketone corresponding to the relevant 2-oxoacetate of formula (I).

[0124] Surfaces suitable for such treatment are, in particular, textiles, hard surfaces, hair and skin.

[0125] The definitions of perfume system and consumer product are the same as those defined above.

[0126] The present invention also relates to a method for enhancing or prolonging the diffusion effect of the characteristic odor of a fragrance component on a surface, characterized in that said surface is treated, preferentially in the presence of light, with a fragrance system as defined above or a perfumed consumer product as defined above under conditions allowing the release of at least aldehydes and / or ketones corresponding to the relevant profragrance (I).

[0127] Suitable surfaces for such treatment are in particular textiles, hard surfaces, hair and skin. Preferred surfaces for such treatment are textiles and hard surfaces.

[0128] The definitions of perfume system and consumer product are the same as those defined above.

[0129] Example The present invention will now be described in more detail by the following examples. In the examples, abbreviations have their usual meaning in the art. Temperatures are given in degrees Celsius (°C). NMR spectral data were obtained on a Bruker AMX500 spectrometer unless otherwise noted. 1 For H, it is 500MHz, 13 C were recorded at 125.8 MHz in CDCl3. Chemical displacements δ are given in ppm relative to Si(CH3)4 as the reference. Coupling constants J are expressed in Hz (br = broad peak). Reactions were carried out in standard glassware under N2. Commercially available reagents and solvents were used without further purification unless otherwise noted. Although specific conformations or configurations are shown for some compounds, this is not meant to limit the use of these compounds to the isomers depicted. According to the present invention, all possible conformational or configurational isomers are expected to have similar effects.

[0130] Example 1 Preparation of compounds according to formula (I) (a) Synthesis of 2-phenylethyl 2-oxo-2-phenylacetate (Compound O1) At 0°C, a solution of N,N'-dicyclohexylcarbodiimide (DCC, 5.54 g, 27 mmol) in dichloromethane (30 mL) was added dropwise to a solution of 4-dimethylaminopyridine (DMAP, 0.28 g, 0.3 mmol), 2-phenylethanol (5.00 g, 41 mmol), and 2-oxo-2-phenylacetic acid (benzoylformic acid, 3.43 g, 23 mmol) in dichloromethane (140 mL). After stirring for 10 minutes, the reaction mixture was allowed to warm to room temperature. After 6 hours, the reaction mixture was filtered through Celite®, extracted with diethyl ether (twice), and washed with water (three times), aqueous HCl (10%, three times), and saturated aqueous NaHCO3. The organic phase was dried (Na2SO4), filtered, and concentrated. Column chromatography (SiO2, n-heptane / diethyl ether 8:2 to 7:3) gave 5.52 g (94%) of the title compound. [ka]

[0131] (b) Synthesis of (E)-oct-2-en-4-yl 2-oxo-2-phenylacetate (Compound O2) Under nitrogen, a dispersion of LiAlH4 (1.8 g, 47.4 mmol) in tetrahydrofuran (THF, 50 mL) was cooled on an ice bath. (E)-Oct-2-en-4-one (10.0 g, 79.2 mmol) in THF (50 mL) was added dropwise over 30 minutes, maintaining the reaction temperature below 5°C. After stirring at room temperature for 1 hour, the mixture was cooled to 0°C in an ice bath, and water (1.8 g) was added very slowly, maintaining the reaction temperature below 7°C. Then, an aqueous solution of NaOH (10%, 1.8 g) and water (5.4 g) were added. The ice bath was removed, and the mixture was stirred for 1 hour. A white precipitate slowly formed. Sodium sulfate (10.0 g) was added, and the reaction mixture was filtered. The THF was removed under reduced pressure (40° C., 4 mbar, 2 h) to give 9.59 g (90%) of (E)-oct-2-en-4-ol. [ka]

[0132] At 0°C, a solution of DCC (8.34 g, 43 mmol) in dichloromethane (25 mL) was added dropwise to a solution of (E)-oct-2-en-4-ol (5.00 g, 39 mmol), 2-oxo-2-phenylacetic acid (8.78 g, 59 mmol), and DMAP (3.81 g, 31 mmol) in dichloromethane (30 mL). The reaction mixture was allowed to warm to room temperature. After stirring for 18 h, the reaction mixture was filtered through sintered glass, rinsed with dichloromethane (20 mL), and concentrated. The residue was dissolved in ethyl acetate (70 mL) and washed with an aqueous solution of HCl (10%, 50 mL), a saturated aqueous solution of NaCl (50 mL), an aqueous solution of NaHCO (10%, 50 mL), and again with a saturated aqueous solution of NaCl (50 mL). The organic phase was dried (NaSO), filtered, and concentrated. Column chromatography (SiO2, n-pentane / ethyl acetate 8:2) gave 7.60 g (75%) of the title compound. [ka]

[0133] Example 2 How to classify fragrance ingredients into Group A and Group B Ethyl 2-oxo-2-phenylacetate (3.0 g L) in non-degassed acetonitrile -1 , Supplier: Alfa Aesar) and the fragrance material to be tested (3.0 g L -1 ) solutions were mixed in GC vials (0.5 mL each) to obtain 1.5 g L -1 Solutions of each component were obtained in a 1:1 weight ratio. All fragrance materials were tested as obtained from commercial sources without further purification. Fragrance materials commercially available as mixtures of isomers were tested as obtained in a 1:1 weight ratio with 2-oxoacetate. Each sample was prepared in duplicate. One sample was kept as a reference (100%), while the other sample was irradiated.

[0134] Light exposure was provided by a Sanalux SAN-40 lamp with a Philips PL-L 36W / 09 / 4P bulb, providing 3.1 mW cm -2 The light energy was monitored with an Ahlborn Almemo 2690-8A measuring device equipped with an FLA603 UV14 UVA sensor. -2 To obtain the desired constant irradiation energy of , the UV lamp was preheated for 1 h and placed at a constant distance relative to the sample.

[0135] The amount of decomposition of ethyl 2-oxo-2-phenylacetate in the presence of selected fragrance raw materials was determined by analytical gas chromatography (GC). The first of the two samples was injected into the GC without irradiation, while the second was irradiated (as outlined above) at 3.1 mW cm. -2 The samples were injected after 40 minutes of irradiation at 100°C. The amount of degradation corresponds to the ratio of the recorded GC peak area obtained for ethyl 2-oxo-2-phenylacetate remaining after 40 minutes of irradiation to the GC peak area of ​​ethyl 2-oxo-2-phenylacetate recorded before irradiation. In the absence of fragrance raw materials, ethyl 2-oxo-2-phenylacetate was found to decompose to 19.9 (±7.6)% under these conditions.

[0136] If the peak area of ​​ethyl 2-oxo-2-phenylacetate recorded after 40 minutes of irradiation in the presence of a given fragrance raw material is reduced to a value of 50% or less relative to the non-irradiated sample, the corresponding fragrance raw material is considered to be part of group A, and if the peak area of ​​ethyl 2-oxo-2-phenylacetate recorded after 40 minutes of irradiation in the presence of a given fragrance raw material is reduced to a value of more than 50%, the corresponding fragrance raw material is considered to be part of group B.

[0137] Analytical GC before and after irradiation was performed on an Agilent Technologies 7890A GC system equipped with an Agilent Technologies 7683B series injector and a flame ionization detector (FID). Samples (5 μL, split ratio 50:1) were ionized in an Agilent HP-5 capillary column (30 m, 0.32 mm inner diameter, 0.25 μm membrane) using helium (2.4 mL min -1 ) at 60°C for 1 minute, then at 10°C for -1 The mixture was heated to 250°C.

[0138] The following results obtained for the screening of various perfume raw materials are summarized in Table 1. [Table 1-1] [Table 1-2] [Table 1-3]

[0139] As can be seen, different perfume ingredients hinder the light-induced decomposition of 2-oxoacetate in different ways: the higher the percentage of ethyl 2-oxo-2-phenylacetate remaining after irradiation, the stronger the influence of each perfume ingredient on the photoreaction, and therefore the less ethyl 2-oxo-2-phenylacetate should be used.

[0140] Example 3 Preparation of model fragrances using Group A and Group B fragrance raw materials The following model fragrances were prepared: [Table 2] [Table 3] [Table 4]

[0141] Example 4 Preparation of Core-Shell Microcapsules A and B Using 2-Oxoacetates of Formula (I) and / or Perfume Raw Materials of Group A and Group B as the Encapsulated Oil Phase Core-shell microcapsules were prepared according to the following general protocol. [Table 5]

[0142] An oil phase was prepared by mixing polyisocyanate (Takenate® D-110N, trimethylolpropane adduct of xylylene diisocyanate, supplied by Mitsui Chemicals) with the core oil. The oil phase consisted of 2% Takenate® D-110N and 98% core oil.

[0143] To prepare the capsule slurry, an acrylamide and acrylic acid copolymer and a blend of two melamine-formaldehyde resins were dissolved in water to form an aqueous phase. The oil phase was then added to this solution, and the pH was adjusted to 5 with acetic acid. The temperature was raised to 80°C over two hours to harden the capsules. A 3% solution of Salcare SC60 (acrylamidopropyltrimonium chloride / acrylamide copolymer) in water was then added to this mixture at 80°C and allowed to react at 80°C for one hour. A solution of ethylene urea (50% by weight in water) was then added to scavenge any remaining free formaldehyde, and the slurry was allowed to cool to room temperature. The final pH was adjusted to 7 with sodium hydroxide.

[0144] Microcapsules C0 were prepared according to the general protocol using 2-phenylethyl 2-oxo-2-phenylacetate (O1, 28.35 g, prepared as described in Example 1a) as the encapsulated oil phase. Flow particle image analysis (FPIA) revealed an average capsule diameter of 13.5 μm, and thermogravimetric analysis (TGA) indicated an oil content of 29.7 wt%.

[0145] Microcapsules C1 were prepared according to the general protocol using a mixture of 2-phenylethyl 2-oxo-2-phenylacetate (O1, 4.71 g) and model fragrance 1 (P1, 23.61 g) as the encapsulated oil phase. FPIA revealed an average capsule diameter of 12.7 μm, and TGA indicated an oil content of 30.4 wt%.

[0146] Microcapsules C2 were prepared according to the general protocol using a mixture of 2-phenylethyl 2-oxo-2-phenylacetate (O1, 7.12 g) and model fragrance 2 (P2, 21.31 g) as the encapsulated oil phase. FPIA revealed an average capsule diameter of 12.8 μm, and TGA indicated an oil content of 28.8 wt%.

[0147] Microcapsules C3 were prepared according to the general protocol using a mixture of 2-phenylethyl 2-oxo-2-phenylacetate (O1, 9.48 g) and model fragrance 3 (P3, 18.95 g) as the encapsulated oil phase and copolymer RSL9500 (supplier: SNF, France) as the acrylamide and acrylic acid copolymer. FPIA revealed an average capsule diameter of 10.2 μm, and TGA indicated an oil content of 29.8 wt%.

[0148] Microcapsules D1 were prepared according to the general protocol using model fragrance 1 (P1, 28.12 g) as the encapsulated oil phase. FPIA revealed an average capsule diameter of 11.0 μm, and TGA indicated an oil content of 28.9 wt%.

[0149] Microcapsules D2 were prepared according to the general protocol using model fragrance 2 (P2, 28.33 g) as the encapsulated oil phase. FPIA revealed an average capsule diameter of 16.1 μm, and TGA indicated an oil content of 28.9 wt%.

[0150] Microcapsules D3 were prepared according to the general protocol using model fragrance 3 (P3, 28.31 g) as the encapsulated oil phase and copolymer RSL9500 (supplier: SNF, France) as the acrylamide and acrylic acid copolymer. FPIA revealed an average capsule diameter of 11.0 μm, and TGA indicated an oil content of 29.1 wt%.

[0151] Further core-shell microcapsules were prepared according to the following protocol.

[0152] Preparation of polyamide microcapsules C4: Sodium caseinate (2.0 g) was dispersed in benzyl benzoate (10.0 g, Group A perfume raw material). The dispersion was stirred at 60°C for 30 minutes, and then 2-phenylethyl 2-oxo-2-phenylacetate (O1, 25.0 g) was added at room temperature. Benzene-1,3,5-tricarbonyl chloride (1.7 g) was solubilized at 60°C for 1 minute. The two oil phases were mixed together, stirred at room temperature for 30 seconds, and then mixed with a solution of L-lysine (2.5 g) in tap water (94.0 g). The reaction mixture was stirred in an Ultra Turrax at 24,000 rpm for 30 seconds to obtain an emulsion. Ethylenediamine (0.12 g) and diethylenetriamine (0.21 g) were dissolved in tap water (5.0 g), and this solution was added dropwise to the emulsion over 5 minutes. The reaction mixture was stirred at 60° C. for 4 hours, resulting in a white dispersion.

[0153] Microcapsules C5 were prepared according to the protocol for the preparation of microcapsules C4, but by replacing benzyl benzoate with 1,2-dimethoxy-4-[(1E)-1-propen-1-yl]benzene (a perfume raw material of Group B).

[0154] Microcapsules containing the 2-oxoacetate of formula (I) are referred to as microcapsules C0, C1, C2, C3, C4, C5, etc., and microcapsules not containing the 2-oxoacetate of formula (I) are referred to as microcapsules D1, D2, D3, etc.

[0155] Example 5 Evaluating the performance of the fragrance system of the present invention by dynamic headspace analysis The fragrance system according to the present invention, containing microcapsules A and / or B and / or free perfume oil, was dispersed in an aqueous solution of sodium lauryl ether sulfate (SLES, 3% by weight, 12.2 g) to obtain a final dispersion containing 5.8 mg of 2-oxoacetate in total. The amount of perfume raw materials in the various dispersions was then adjusted to always correspond to the same ratio relative to the amount of 2-oxoacetate. For example, microcapsule C1 contained 30.4% by weight of oil composed of 16.6% 2-phenylethyl 2-oxo-2-phenylacetate (O1) and 83.4% model fragrance 1 (P1, consisting of five perfume raw materials, each at 16.6%). Thus, a dispersion obtained from 114.1 mg of microcapsule C1 and 12.2 g of SLES contained 5.8 mg of 2-phenylethyl 2-oxo-2-phenylacetate and 28.9 mg of model fragrance 1. Equivalent dispersions containing the same total amounts of 2-phenylethyl 2-oxo-2-phenylacetate (5.8 mg) and model fragrance 1 (28.9 mg) were prepared by adding microcapsule C0 (19.5 mg) and microcapsule D1 (100.0 mg) to 12.2 g of SLES, or by adding free 2-phenylethyl 2-oxo-2-phenylacetate (5.8 mg) and microcapsule D1 (100.0 mg) to 12.2 g of SLES. Other samples were prepared accordingly.

[0156] The dispersion (250 mg) was then pipetted onto a glass slide (13 × 4 cm) and allowed to dry overnight in the dark. Each glass plate was then covered with a second glass plate. The two plates were rubbed against each other by pressing firmly against each other while moving from left to right five times and from top to bottom five times. The two plates were then separated and placed in a homemade headspace sampling cell (625 mL) by facing the lamp. The dispersion was filtered through activated carbon and humidified with a saturated aqueous solution of NaCl in 200 mL min. -1 A stream of air was drawn through the cell. The system was allowed to equilibrate for 10 minutes by adsorbing the volatiles onto a waste poly(2,6-diphenyl-p-phenylene oxide) (Tenax® TA, 100 mg) cartridge, followed by 5 minutes on a clean cartridge (first data point). The lamp was turned on, and the volatiles were adsorbed onto the waste Tenax® for 5 minutes, followed by 5 minutes on a clean Tenax® cartridge (data points 2-6). The volatiles were then adsorbed onto the waste Tenax® cartridge for 5 minutes and then onto a clean Tenax® cartridge for 5 minutes (three times, data points 7-9). Finally, the volatiles were adsorbed onto the waste Tenax® cartridge for 25 minutes and then onto a clean Tenax® cartridge for 5 minutes (data point 10). The waste Tenax® cartridge was discarded, and the clean Tenax® cartridge was transferred to an Agilent GC / MS instrument equipped with an FID. Volatiles were desorbed on a Perkin Elmer TurboMatrix ATD thermodesorber connected to a Technologies 7890A GC system. Volatiles were desorbed on a HP-5 capillary column (30 m × 0.32 μm, 0.25 μm membrane) at 15 °C for 1 min. -1 The elution was performed with He using a temperature gradient from 60°C to 200°C or 260°C. The headspace concentration (ngL -1) was obtained by external standard calibration by injecting solutions of known amounts of volatiles onto clean Tenax® cartridges and allowing them to release as previously described.

[0157] Light irradiation was performed using a UVA lamp (360 nm) at 1.6 mW cm -2 This was checked with an Ahlborn Almemo 2690-8A measuring device connected to an FLA603 UV14 UVA sensor.

[0158] The aromatic systems listed in the table below were prepared as outlined above and exposed to light (1.6 mW cm -2 The fragrances were evaluated on glass slides by dynamic headspace analysis under UVA light (at 1000 Hz). The values ​​in brackets indicate the amount of fragrance raw material from Group B for each part of the fragrance system. The headspace concentrations of the released scents from the 2-oxoacetate derivatives of formula (I) as part of the various fragrance systems recorded after 35 minutes (= 20 minutes after irradiation, data point 4) are shown. [Table 6]

[0159] Headspace analysis showed that the various scent ingredients of the model fragrances essentially evaporated slowly (at higher headspace concentrations) when they were encapsulated (and thus released by rubbing prior to the experiment) and more rapidly (at lower headspace concentrations) when they were part of the free perfume oil, and thus were able to evaporate overnight. Under these conditions, the evaporation of the scent ingredients was not significantly affected by light-induced cleavage of the 2-oxoacetate.

[0160] On the other hand, the light-induced generation of 2-phenylacetaldehyde from 2-phenylethyl 2-oxo-2-phenylacetate (O1) was dependent on the presence of fragrance raw materials from Group B. The headspace concentrations of 2-phenylacetaldehyde measured for the various fragrance systems outlined above are summarized in Figure 1.

[0161] Figure 1 shows the dynamic headspace concentration of 2-phenylacetaldehyde produced from 2-phenylethyl 2-oxo-2-phenylacetate (O1) upon irradiation of various fragrance systems containing varying amounts of Group B fragrance raw materials (indicated in parentheses) in microcapsules A or B or free perfume oil (P). The open symbols and solid line represent the formation of 2-phenylacetaldehyde in the presence of model fragrance 1 (P1), which contains less than 30% Group B fragrance raw materials; the closed symbols and solid line represent the formation of 2-phenylacetaldehyde in the presence of model fragrance 2 (P2), which contains more than 30% Group B fragrance raw materials; and the open symbols and dashed line represent the formation of 2-phenylacetaldehyde in the presence of model fragrance 1 (P3), which contains no Group B fragrance raw materials (0%).

[0162] The data in Figure 1 show that fragrance systems containing more than 30% Group B fragrance raw materials (black symbols and solid line) release significantly less 2-phenylacetaldehyde from 2-phenylethyl 2-oxo-2-phenylacetate than fragrance systems containing less than 30% Group B fragrance raw materials (white symbols and solid line), and release significantly less 2-phenylacetaldehyde than fragrance systems containing no Group B fragrance raw materials (white symbols and dashed line). Furthermore, the Group B fragrance raw materials are dispersed in microcapsules A (diamonds, e.g., [ka] ) or B (square, e.g. [ka] ), rather than being encapsulated in a pellet, a portion of the perfume oil in a free state (e.g., [ka] ) is found to be part of

[0163] As a further reference, irradiation of 2-phenylethyl 2-oxo-2-phenylacetate (O1) alone under the same conditions produced 300.8 ng / L of 2-phenylacetaldehyde after 35 minutes of sampling (data not shown in Figure 1), a value in the same order as that recorded for a fragrance system that did not contain encapsulated fragrance ingredients from Group B (see entry 12 in the table above).

[0164] Irradiation of a fragrance system consisting of 2-oxoacetate O2 and microcapsules D3, which did not contain any fragrance raw materials from Group B and were prepared and irradiated under the same conditions as described above, showed a strong release of (£)-oct-2-en-4-one (see entry 13 in the table above). Again, the recorded headspace concentration of (£)-oct-2-en-4-one released from this fragrance system was of the same order of magnitude as that measured for irradiation of 2-oxoacetate O2 alone (2937.9 ng / L after 35 minutes of sampling). This demonstrates that various 2-oxoacetates of formula (I) that release different perfume aldehydes or ketones can be used to prepare fragrance systems.

[0165] It should be noted that the absolute headspace concentrations of scent released upon light irradiation from structurally different 2-oxoacetates of formula (I) will vary from compound to compound, and therefore comparisons should be made within a series using the same compound of formula (I).

[0166] Example 6 Evaluating the performance of the fragrance system of the present invention by dynamic headspace analysis The fragrance system containing microcapsules A according to the present invention was dispersed in an aqueous solution of sodium lauryl ether sulfate (SLES, 3% by weight, 12.2 g) to give a total of 5.7 mg of 2-oxoacetate in the final dispersion. 250 mg of this dispersion was then pipetted onto a glass slide (13 x 4 cm) and treated as described in Example 5.

[0167] The fragrance systems listed in the table below were prepared as outlined in Example 5 and exposed to light irradiation (1.6 mW cm -2 The data were analyzed by dynamic headspace analysis on glass slides under UVA light (at 1000 Hz). The values ​​in brackets indicate the amount of Group B fragrance raw material for each part of the fragrance system. The headspace concentrations of 2-phenylacetaldehyde released from 2-oxoacetate O1 as part of the various fragrance systems recorded after 35 minutes (= 20 minutes after irradiation, data point 4) are shown. [Table 7]

[0168] Figure 2 shows the dynamic headspace concentration of 2-phenylacetaldehyde produced from 2-oxoacetate O1 upon light irradiation of various fragrance systems containing 0% or 29% (indicated in parentheses) of Group B perfume raw materials in microcapsules A.

[0169] The data show that the presence of Group B fragrance ingredients resulted in lower headspace concentrations of 2-phenylacetaldehyde released into the headspace than comparable samples that did not contain Group B fragrance ingredients.

[0170] Example 7 Preparation of Liquid Detergent Formulations Containing the Fragrance System of the Present Invention As a non-limiting example, a fragrance system according to the present invention, such as that described in Example 5 or Example 6, is dispersed under gentle shaking in a liquid detergent formulation having the typical composition described below to obtain a total amount of encapsulated and free perfume oil of 0.10 to 0.80% in the final product. [Table 8]

[0171] Example 8 Preparation of Fabric Softener Formulations Containing the Fragrance System of the Present Invention As a non-limiting example, a fragrance system according to the present invention, such as that described in Example 5 or Example 6, is dispersed under gentle shaking in a fabric softener formulation having the typical composition described below to obtain a total amount of 0.20-0.80% of encapsulated and free perfume oil in the final product. [Table 9]

[0172] Example 9 Preparation of All-Purpose Cleaner Formulations Containing the Fragrance System of the Present Invention As a non-limiting example, a fragrance system according to the present invention, such as that described in Example 5 or Example 6, is dispersed under gentle shaking in an all-purpose cleaner formulation having the typical composition described below to obtain a total amount of encapsulated and free fragrance oil of 0.30-0.80% in the final product. [Table 10]

[0173] Example 10 Preparation of Hand Dishwashing Formulations Comprising the Fragrance System of the Present Invention A typical unperfumed hand dishwashing formulation is prepared from the ingredients listed below by combining water with sodium hydroxide and diethanolamide. Linear alkylbenzene sulfonic acid is then added. After neutralization, the remaining ingredients are added and the pH is adjusted to 7-8, if necessary. [Table 11]

[0174] As a non-limiting example, a fragrance system according to the present invention, such as that described in Example 5 or Example 6, is dispersed under gentle shaking in an unperfumed hand dishwashing formulation having the typical composition described above to obtain a total amount of 0.10-1.00% encapsulated and free fragrance oil in the final product.

Claims

1. a) core-shell microcapsules A; b) optionally, core-shell microcapsules B; c) optionally, perfume oil in free form; Including, The core of the core-shell microcapsules A and / or the perfume oil in free state may be a compound of formula (I) 【Chemistry 1】 [In the formula, R １ is a straight or branched chain C optionally containing 1 to 4 oxygen atoms that are not directly attached to a carbonyl group １ ~C ２２ A cyclic C group optionally containing 1 to 4 oxygen atoms that are not directly bonded to an alkyl or alkenyl group, or a carbonyl group. ３ ~C ８ an alkyl or alkenyl group, or C １ ~C ４ represents a phenyl group optionally substituted with an alkyl group, R ２ is a straight, branched or cyclic C optionally containing 1 to 4 oxygen atoms １ ~C ２２ represents a hydrocarbon group, R ３ represents a hydrogen atom or C optionally containing 1 to 2 oxygen atoms １ ~C １０ represents a hydrocarbon group, or R ２ and R ３ Together, C ５～１６ Cycloalkyl group, C ５～１６ Cycloalkenyl group, C ４～１４ Heterocycloalkyl group or C ４～１４ forming a heterocycloalkenyl group] and a 2-oxoacetate derivative of The core of the core-shell microcapsule A is optionally at least one perfume raw material of group A, - maximum 20% by weight of Group B perfume raw materials, and optionally, a solvent Including, The core of the core-shell microcapsule B is - at least one perfume raw material of group A, - maximum 30% by weight of Group B perfume raw materials, and optionally, a solvent Including, Group A perfume raw materials are defined as those in which no more than 50% of ethyl 2-oxo-2-phenylacetate (used as a reference compound) remains after irradiation of said perfume raw material and 2-oxoacetate (1.5 g L −1 ) in a 1:1 weight ratio in non-degassed acetonitrile with UVA radiation at 3.1 mW cm −2 at 25° C. for 40 minutes; Group B perfume raw materials are defined as those in which, after irradiation of said perfume raw material and 2-oxoacetate (1.5 g L −1 ) in a 1:1 weight ratio in non-degassed acetonitrile with UVA radiation at 3.1 mW cm −2 at 25° C. for 40 minutes, more than 50% of ethyl 2-oxo-2-phenylacetate (used as a reference compound) remains; and the amount of Group A perfume raw materials in the fragrance system is at least 70% by weight and the amount of Group B perfume raw materials in the fragrance system is less than 30% by weight, based on the total weight of the fragrance system; The perfume raw materials of Group B are encapsulated in a minimum amount in core-shell microcapsules A or B or in free perfume oil. Aromatic.

2. The core of the core-shell microcapsule A is at least one 2-oxoacetate derivative of formula (I) in an amount of at least 50% by weight 2. The aromatic system of claim 1, comprising:

3. 3. The fragrance system according to claim 1, wherein the core of the core-shell microcapsule A does not contain any perfume raw material of group B.

4. The perfume oil in its free state - at least one perfume raw material of said group A, optionally at least one perfume raw material of said group B, optionally at least one 2-oxoacetate derivative of formula (I) and optionally, a solvent 4. The aromatic system according to claim 1, comprising:

5. 5. The fragrance system according to claim 1, wherein the free perfume oil comprises up to 50% by weight of Group B perfume raw materials.

6. 6. A fragrance system according to any one of claims 1 to 5, wherein the perfume oil in free state comprises 0.1 to 20% by weight of the 2-oxoacetate derivative of formula (I).

7. 7. The fragrance system according to claim 1, wherein the core of the core-shell microcapsule A and the core of the core-shell microcapsule B do not contain perfume raw materials of Group B.

8. The perfume raw materials of Group A include allyl 2-(cyclohexyloxy)acetate, allyl 3-cyclohexylpropanoate, allyl heptanoate, allyl hexanoate, benzaldehyde, benzyl acetate, benzyl benzoate, benzyl 2-hydroxybenzoate, 2-cyclohexylethyl acetate, cyclohexyl 2-hydroxybenzoate, 4-cyclohexyl-2-methyl-2-butanol, decanal, diethyl 1,4-cyclohexanedicarboxylate, (2,2-dimethoxyethyl)benzoate, zene, 6,6-dimethoxy-2,5,5-trimethyl-2-hexene, 2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl acetate, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 2,6-dimethyl-2-heptanol, 2,6-dimethyl-5-heptenal, 6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane, 3,7-dimethyl-2,6- and 3,6-nonadienes octenenitrile, 3,7-dimethyl-1,6-nonadien-3-ol, 3,7-dimethyl-2,6-octadienal, (E)-3,7-dimethyl-2,6-octadienol, (Z)-3,7-dimethyl-2,6-octadienol, 3,7-dimethyl-1,6-octadien-3-ol, 3,7-dimethyl-2,6-octadienyl acetate, 3,7-dimethyl-3-octanol, 3,7-dimethyl-6-octenenitrile, 3,7-dimethyl-6-octen-1-ol, 2,6-dimethyl-7-octen-2-ol ol, 3,7-dimethyl-6-octenyl acetate, 1,1-dimethyl-2-phenylethyl butanoate, 1,1-dimethyl-2-phenylethyl acetate, 3,3-dimethyl-5-[2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 1,4-dioxacycloheptadecane-5,17-dione, dodecanal, dodecanol, (Z)-4-dodecenal, ethyl butanoate, ethyl 3-hydroxybut-2-enoate, ethyl 2-methylbutanoate, ethyl 2-methyl-1,3-Dioxolane-2-acetate, ethyl 2-methylpentanoate, ethyl 3-oxobutanoate, 3-(2- and 4-ethylphenyl)-2,2-dimethylpropanal, (2E)-2-ethyl-4-[2,2,3-trimethyl-3-cyclopenten-1-yl]-2-buten-1-ol, 6-ethyl-2,10,10-trimethyl-1-oxaspiro[4.5]deca-3,6-diene, 5-heptyldihydro-2(3H)-furanone, 4,6 , 6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethanone, (Z)-3-hexen-1-ol, (Z)-3-hexenyl acetate, (Z)-3-hexenyl 2-hydroxybenzoate, hexyl acetate, 5-hexyldihydrofuran-2(3H)-one, hexyl 2-hydroxybenzoate benzoate, hexyl 2-methylpropanoate, 3- and 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 1-isopropyl-4-methylbenzene, 2-isopropyl-5-methylcyclohexan-1-ol, isopropyl 2-methylbutanoate, 4-isopropyl-1-methylcyclohexyl acetate, 3-(3-isopropyl-1-phenyl)butanal, 3-(4-isopropylphenyl)-2 -methylpropanal, isopropyl tetradecanoate, 4-methoxybenzaldehyde, 1-methoxy-4-methylbenzene, 3-(4-methoxyphenyl)-2-methylpropanal, 4-(2-methoxy-2-propanyl)-1-methylcyclohexene, 1-methoxy-4-(2-propenyl)benzene, 6-methoxy-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulene, methyl benzoate, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 3-methyl-2-buten-1-yl acetate, 2- and 3-methylbutyl acetate, 2- and 3-methylbutyl butyrate, 2-methylbutyl 2-hydroxybenzoate, 2-(4-methylcyclohex-3-enyl)propan-2-ol, 2-(4-methyl-3-cyclohexen-1-yl)-2-propanyl acetate, 2-{2-[4-methyl-3-cyclohexen-1-yl]propyl}cyclopentanone, (E)-4-methyl-3-decen-5-ol, methyl 2,2-di Methyl-6-methylidenecyclohexanecarboxylate, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 5-methylheptan-3-one oxime, methyl 7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylate and methyl 7-isopropyl-1,4a-dimethyltetradecahydrophenanthrene-1-carboxylate, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde , 2-methyl-3-[4-(2-methyl-2-propanyl)phenyl]propanal, 4-methyl-2-(2-methyl-1-propen-1-yl)tetrahydro-2H-pyran, methyl 2-octinoate, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 4-methyl-4-penten-2-yl 2-methylpropanoate, 3-methyl-5-phenyl-1-pentanol, 5-methyl-2-(2-propanyl)cyclohexanone, 1-methyl-4-(2-propanyl)-1,4-cyclohexadiene, 4-(2-methyl- 2-propanyl)cyclohexanol, 2-(2-methyl-2-propanyl)cyclohexyl acetate, 4-(2-methyl-2-propanyl)cyclohexyl acetate, 1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene, 2-methyl-4-propyl-1,3-oxathiane, (3E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohex-1-yl)-3-buten-2-one, methyl 2,6,6-trimethyl-3-cyclohexene-1-carboxylate, (3E)-3-methyl-4-(2,6,(1E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol, 2-methylundecanal, 2,6-nonadienal, 2,6-nonadienol, nonanal, octanal, oct-2-en-4-one, oxacyclohexadecan-2-one, 1-oxa-12- and 13-cyclohexadecen-2-one, 1,1'-oxacyclohexadecan ... Dibenzoylbenzene, pentyl 2-hydroxybenzoate, 2-phenoxyethanol, 2-phenylacetaldehyde, 3-phenylbutanal, 2-phenylethanol, 2-phenylethyl acetate, phenylmethanol, 4-[(2-propanyl)cyclohexyl]methanol, 7-propyl-2H-benzo[b][1,4]dioxepin-3(4H)-one, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, 3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 1-(3,6,8,8-tetramethyl 1-(2,3,8,8-tetramethyl-1,2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulen-5-yl)ethan-1-one, 2,3,6,7- and 2,4,6,8-tetramethylnonan-1-ol, 3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-yl acetate, 2,2,6,8-tetramethyl-1,2,3,4,4a,5,8,8a-octahydro-1-naphthalenol, 1-(2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-, 1,2,3,5,6,7,8,8a- and 1,2,3,4,6,7 ,8,8a-octahydronaphthalen-2-yl)ethan-1-one, tricyclo[5.2.1.0(2,6)]dec-3- and 4-en-8-yl acetate, 2,2,2-trichloro-1-phenylethyl acetate, tricyclo[5.2.1.0(2,6)]dec-3- or 4-en-8-yl propanoate, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate, 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene, 2-(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)-1-cyclohexanol, 2-, 3- and 4-(5,5,6-trimethylbicyclo[2.2.1]hept-2-yl)-1-cyclohexanol, (2E)-1-[2,6,6-trimethyl-1-cyclohexen-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-cyclo The aromatic system according to any one of claims 1 to 7, which is selected from the group consisting of (hexen-1-yl)-2-buten-1-one, 3,8,9-, 4,6,8- and 4,7,9-trimethyldecan-2-ol, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 2,2,5-trimethyl-5-pentylcyclopentanone, 2,6,6-trimethylspiro[bicyclo[3.1.1]heptane-3,1'-cyclohexane]-2'-en-4'-one, undecanal, 1,3,5-undecatriene and 10-undecenal.

9. The fragrance raw materials of Group B include benzo[d][1,3]dioxole-5-carbaldehyde, (E)-1-(benzyloxy)-2-methoxy-(4-prop-1-en-1-yl)benzene, 2H-chromen-2-one, 1,2-dimethoxy-4-[(1E)-1-propen-1-yl]benzene, 1,5-dimethyl-1-vinyl-4-hexenyl(E)-3-phenylpropenoate, (E)-2-hexyl-3-phenyl-2-propenal, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, 2-isobutylquinoline, 2-methoxynaphthalene, 2-methoxy-4-(2-propen-1-yl)phenol, 2-methoxy-4-[(1E)-1-propen-1-yl]phenol, 2-methoxy-4-propylphenol, methyl ...

9. The aromatic system according to claim 1, wherein the aromatic compound is selected from the group consisting of methyl 2-aminobenzoate, methyl N-[3-(4-tert-butylphenyl)-2-methyl-1-propenyl]anthranilate, methyl 2-(methylamino)benzoate, 6-methyl-1,2,3,4-tetrahydroquinoline, 1-(naphthalen-2-yl)ethan-1-one, (E)-2-pentyl-3-phenyl-2-propenal, (Z)-2-phenyl-2-hexenenitrile, (E)-3-phenyl-2-propen-1-ol, (2E)-1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one and (3E)-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one.

10. i. an aromatic system according to any one of claims 1 to 9; ii. at least one ingredient selected from the group consisting of a perfume carrier and a perfume base; iii. Optionally, at least one flavor adjuvant; A perfume composition comprising:

11. A perfumed consumer product comprising an aroma system according to any one of claims 1 to 9, characterized in that it is a fragrance, a fabric care product, a body care product, an air care product or a home care product.

12. 12. The perfumed consumer product of claim 11, characterized in that the perfumed consumer product is a fine perfumery, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a shampoo, a coloring formulation, a hairspray, a deodorant or antiperspirant, a perfumed soap, a shower or bath smoothie, an oil or gel, a hygiene product, an air freshener, a "ready to use" powder air freshener or a hard surface cleaner.

13. 10. Use of an aroma system according to any one of claims 1 to 9 for enhancing, imparting, improving and / or modifying the scent profile and / or scent intensity of a perfumed consumer product.

14. 10. A method for enhancing, imparting, improving and / or modifying the scent profile and / or scent intensity by applying an aroma system according to any one of claims 1 to 9 to a perfumed consumer product.

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