Fragrance composition containing 2-(alkylsulfonyl)octan-4-one

Abstract

The present invention relates to a fragrance composition comprising a 2-(alkylsulfonyl)octan-4-one compound of formula (I) and an oil phase comprising at least one perfume raw material, wherein the compound of formula (I) is present in an amount of at least 5% by weight in the fragrance composition. The present invention further relates to a method for producing the fragrance composition and to a consumer product comprising the fragrance composition.

Description

[Technical Field]

[0001] The present invention relates to a fragrance composition comprising a 2-(alkylsulfonyl)octan-4-one compound of formula (I) and an oil phase containing a perfume raw material, wherein the compound of formula (I) is present in an amount of at least 5% by weight in the fragrance composition. The present invention further relates to a method for producing the fragrance composition and to a consumer product comprising the fragrance composition. [Background technology]

[0002] Consumers often associate the effectiveness of perfumed articles with the long-lasting or persistent fragrance perception. Perfumes are composed of many different volatile compounds that are applied to surfaces and evaporate from them to be smelled. Perfumes are applied to surfaces such as hard surfaces, fabrics, skin, or hair through perfume compositions or perfumed consumer articles, for example, as fine fragrances or various cleaning and cleaning agents. Due to the high volatility of the fragrances that make up perfumes, the scent emitted from the perfumed surface can only be perceived for a limited period of time. In particular, the so-called top notes of perfumes evaporate fairly quickly. They are the most volatile compounds in the composition and represent the freshness of the perfume. Top notes typically include citrus, flowery, green, and fruity notes, among others, and fruity notes are particularly highly valued by consumers. Several classes of fruity notes are used in perfumery, and one example is a note resembling red berries such as raspberry or strawberry. Oct-2-en-4-one can be used as a perfume ingredient to impart a natural strawberry scent when used in perfume compositions or scented consumer articles. However, this compound is quite volatile, and the scent imparted to surfaces such as hard surfaces, fabrics, skin, or hair lasts for a relatively short period of time.

[0003] Consumers desire fragrances that are stable in their intended use, yet have long-lasting and / or persistent odor for hours or even days after application, and long-lasting red berry notes, such as strawberry notes, are particularly desirable.

[0004] For this purpose, pro-fragrances such as 2-(alkylsulfonyl)octan-4-one compounds can be used, which slowly generate oct-2-en-4-one over time and thus impart a long-lasting strawberry scent to the environment (see WO 2019 / 243369).

[0005] 2-(Alkyl sulfonyl)octan-4-one compounds can be advantageously used in fragrance compositions such as fragrance oils. However, this class of compounds is not always easily soluble in fragrance oils. As an example, 2-(dodecyl sulfonyl)octan-4-one is solid at room temperature, and therefore, handling of this compound differs from that of typical fragrance raw materials. One option is to melt the compound above its melting point (49-51°C) before mixing with the fragrance oil; however, 2-(dodecyl sulfonyl)octan-4-one tends to resolidify quickly when the temperature drops below its melting point. Another option is to directly combine the solid 2-(alkyl dodecyl sulfonyl)octan-4-one with the fragrance oil, which requires efficient stirring and / or heating for uniform mixing and complete solubilization.

[0006] To overcome the above-mentioned problems, the 2-(alkylsulfonyl)octan-4-one compound may be provided in the form of a solution, i.e., the 2-(alkylsulfonyl)octan-4-one compound may be dissolved in a solvent.

[0007] However, if the 2-(alkylsulfonyl)octan-4-one compound is first dissolved in a solvent before being added to the fragrance composition, the compound is provided in a diluted form, and a reduced amount of the compound is unavoidable. To at least partially reduce the effect of this dilution, a high concentration of the 2-(alkylsulfonyl)octan-4-one compound in solution is desirable. To ensure that the olfactory impact of the 2-(alkylsulfonyl)octan-4-one compound in the final application is sufficiently large, the fragrance composition should contain the 2-(alkylsulfonyl)octan-4-one compound at a level of at least 5% by weight.

[0008] However, the inventors of the present invention have found that providing a solvent system that meets the above-mentioned requirements is not a trivial matter. In particular, the inventors of the present invention have found that solvents commonly used in the art to dissolve fragrances and pre-fragrances, such as dipropylene glycol (DIPG) or isopropyl myristate (IPM), are unable to completely dissolve the required concentration of 2-(alkylsulfonyl)octan-4-one compounds at room temperature. Therefore, the object of the present invention was to find a solvent that can dissolve a large amount of 2-(alkylsulfonyl)octan-4-one compounds at room temperature, so that an olfactory-sufficient amount of 2-(alkylsulfonyl)octan-4-one compounds can be used in perfume compositions. [Brief explanation of the drawings]

[0009] [Figure 1] Figure 1 shows the solubility of 2-(dodecylsulfonyl)octan-4-one in various liquid carriers and oil phases as a function of temperature. Black triangles: DIPG, grey squares: IPM, open diamonds: Hedione®, black circles: gamma-nonalactone and Cetiol® Ultimate (80 / 20). The solid line represents an exponential fit to the experimental data.

[0010] overview The present invention provides a fragrance composition, comprising: - expression [ka] [wherein n is an integer between 1 and 9] and a 2-(alkylsulfonyl)octan-4-one compound of the formula: an oil phase comprising at least one perfume raw material; Including, The compound of formula (I) is present in the perfuming composition in an amount of at least 5% by weight. The present invention relates to a fragrance composition.

[0011] Another aspect of the present invention relates to a method for producing a perfume composition according to the present invention, comprising the step of dissolving a 2-(alkylsulfonyl)octan-4-one compound of formula (I) in an oil phase comprising at least one perfume raw material.

[0012] The present invention further relates to the use of at least one perfume raw material to dissolve the 2-(alkylsulfonyl)octan-4-one compound of formula (I).

[0013] Furthermore, the present invention relates to consumer products comprising the perfuming composition according to the present invention.

[0014] Detailed Description The present invention provides a fragrance composition, comprising: - expression [ka] [wherein n is an integer between 1 and 9] and a 2-(alkylsulfonyl)octan-4-one compound of the formula: an oil phase comprising at least one perfume raw material; Including, The compound of formula (I) is present in the perfuming composition in an amount of at least 5% by weight. The present invention relates to a fragrance composition.

[0015] By "oil phase" is meant an ingredient or composition that is liquid at about 20°C and that is immiscible or only sparingly miscible with the aqueous phase.

[0016] In certain embodiments, the perfuming composition consists of a compound of formula (I) and an oil phase.

[0017] According to the present invention, the perfuming composition comprises a 2-(alkylsulfonyl)octan-4-one compound of formula (I).

[0018] The compounds according to formula (I) can act as pro-fragrance compounds because they can slowly produce oct-2-en-4-one over time and thus impart a long-lasting strawberry scent to the environment. The expression "strawberry scent" or "strawberry note" is understood to mean an odor reminiscent of strawberry fruit.

[0019] The compound according to formula (I) itself is non-volatile and essentially odorless. The production of oct-2-en-4-one from the compound of formula (I) may be triggered by one or more of the following triggers: the presence of moisture / oxygen, a change in pH, the presence of an enzyme, and an increase in temperature.

[0020] According to the present invention, the integer n in formula (I) is 1-9.

[0021] In certain embodiments, n is 1. In other embodiments, n is 2. In other embodiments, n is 3. In other embodiments, n is 4. In other embodiments, n is 5. In other embodiments, n is 6. In other embodiments, n is 7. In other embodiments, n is 8. In other embodiments, n is 9.

[0022] In a preferred embodiment, the integer n is 3 to 7. Preferably, the integer n is 4 to 6. More preferably, n is 5. When n is 5, the compound of formula (I) is 2-(dodecylsulfonyl)octan-4-one. Thus, in a preferred embodiment, the compound of formula (I) is 2-(dodecylsulfonyl)octan-4-one.

[0023] In certain embodiments, the perfuming composition comprises more than one compound according to formula (I).

[0024] In one embodiment, the perfume composition comprises 1 to 5 compounds of formula (I).

[0025] In one embodiment, the perfuming composition comprises one compound of formula (I).

[0026] In one embodiment, the perfuming composition comprises two compounds of formula (I).

[0027] In one embodiment, the perfume composition comprises three compounds of formula (I).

[0028] In one embodiment, the perfume composition comprises four compounds of formula (I).

[0029] In one embodiment, the perfume composition comprises five compounds of formula (I).

[0030] According to the present invention, the perfuming composition comprises an oil phase containing at least one perfume raw material.

[0031] In a preferred embodiment, the compound of formula (I) is completely dissolved in the oil phase at a temperature of 25° C. Thus, in said preferred embodiment, the oil phase is capable of completely dissolving the compound of formula (I) at a temperature of 25° C.

[0032] Those skilled in the art are familiar with suitable means for determining whether the compound of formula (I) is completely dissolved in the oil phase. For example, a light beam can be passed through a sample of the dissolved compound at 25°C. When 100% light transmittance is achieved, it can be assumed that the compound of formula (I) is completely dissolved in the oil phase at 25°C. The light beam can be based on LED light. Thus, in certain embodiments, the complete dissolution of the compound of formula (I) is determined based on complete light transmittance at 25°C. For measurement, the dissolved sample can be in a glass vial.

[0033] The term "solubility at 25°C" is intended to refer to the thermodynamic equilibrium solubility of the compound of formula (I) at 25°C. Those skilled in the art are well aware that the solubility of any solid compound can increase significantly with increasing temperature of the solvent system. If the temperature is subsequently returned to a lower temperature, for example, 25°C, the solid compound may still remain in solution for a certain period of time while supersaturated. However, this is an apparent solubility due to a non-equilibrium metastable state with limited shelf-life stability, and therefore must be distinguished from the thermodynamic solubility at equilibrium. Thermodynamic solubility can be determined, for example, using the so-called shake-flask method at a controlled temperature. Alternatively, it can be determined by slowly heating the compound and recording the solubilization temperature after complete dissolution.

[0034] In certain embodiments, the oil phase is capable of completely dissolving the compound of formula (I).

[0035] In certain embodiments, the oil phase consists of at least one perfume raw material.

[0036] In certain embodiments, the perfume composition comprises an oil phase in an amount of 95% by weight or less, hi some embodiments, the perfume composition comprises an oil phase in an amount of 90% by weight or less, 80% by weight or less, 70% by weight or less, 60% by weight or less, or 50% by weight or less.

[0037] In certain embodiments, the perfuming composition comprises an oil phase in an amount of 50 to 95% by weight, such as 60 to 95% by weight, or 70 to 95% by weight, or 80 to 95% by weight, or 85 to 95% by weight.

[0038] According to the present invention, the oil phase comprises perfume raw materials.

[0039] A "perfume compound" or "perfume raw material (PRM)" is a compound used as an active ingredient in a perfume composition to impart a hedonic effect. In other words, to be considered a perfume compound, 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 in a positive or pleasant way, rather than simply having an odor.

[0040] The nature and type of perfume raw materials present in the perfume composition of the invention do not warrant a more detailed description (which would in any case not be exhaustive), and those skilled in the art can select them on the basis of their general knowledge and according to the intended use or application and the desired organoleptic effect. In general terms, these perfume raw materials belong to various chemical classes such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, thiols, terpenoids, nitrogen- or sulfur-containing heterocyclic compounds and essential oils, and they may be of natural or synthetic origin.

[0041] Many of these perfume ingredients are listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, NJ, USA, or its more recent editions, or other works of a similar nature, such as Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press, or Synthetic Food Adjuncts, 1947, by M.B. Jacobs, Van Nostrand Co., Inc., as well as in the extensive patent literature in the field of perfumery.

[0042] Fragrance ingredients include, for example: Aldehyde components: (2E)-2-benzylidene octanal, 4-methoxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, 3,7-dimethyl-2,6-octadienal, 2,6-dimethylhept-5-enal, (E)-2-pentyl-3-phenyl-2-propenal, 4-hydroxy-3-methoxybenzaldehyde, benzo[d][1,3]dioxole-5-carbaldehyde, benzaldehyde, (E)-3-phenyl-2-propenal, 3-(2 / 4-ethylphenyl)-2,2-dimethylpropanal, (2E)-2-methyl-3-phenyl-2-propenal, (2E)-2-benzylidene octanal, (+ / - )-1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, (2E)-2-dodecenal, (2E,6Z)-2,6-nonadienal, 4-(2-propanyl)benzaldehyde, 4-methylbenzaldehyde, 4-formyl-2-methoxyphenyl 2-methylpropanoate, (3,4-dimethoxybenzylidene)(methyl)-λ3-oxidane, (2E,6Z)-2,6-nonadienal, (E)-2-decenal, (E)-2-tridecenal, 3,6,7-trimethyl-2,6-octadienal, decanal, 10-undecenal, 2-methylundecanal, and 2-hydroxybenzaldehyde; Aromatic herbal ingredients: camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undecane-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or alpha-pinene; Balsam ingredients: coumarin, ethyl vanillin and / or vanillin; Citrus ingredients: dihydromyrcenol, citral, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthadiene; Floral ingredients: Methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexylcinnamic aldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta-ionone, methyl 2-(methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-penten-3-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 2,5-dimethyl-2-indanethanol, 2,6,6-trimethyl-3-cyclo Hexene-1-carboxylate, 3-(4,4-dimethyl-1-cyclohexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, vergyl acetate, geraniol, p-mentha-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, high cis methyldihydro Jasmonate, 3-methyl-5-phenyl-1-pentanol, vergyl proprionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthanol, propyl (S)-2-(1,1-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamic aldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, vergyl isobutyrate and / or a mixture of methyl ionone isomers; Fruity ingredients: Gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiane, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allylheptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1,3-dioxolane-2-acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal, dimethicone ethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl[3-ethyl-2-oxiranyl]acetate, 4-(4-hydroxyphenyl)butan-2-one, oct-2-en-4-one, 2,5-dimethyl-4-hydroxy-2H-furan-3-one, ethyl 3-methyl-3-phenyloxirane-2-carboxylate and / or diethyl 1,4-cyclohexanedicarboxylate; Green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy) acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one; Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13-cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethylpropionate 3-methyl-5-cyclopentane tadecen-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropylpropanoate, oxacyclohexadecan-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methylpropanoate; Woody Ingredients: 1-[(1RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-5-[(1R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.02,7]undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalene) (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-1-ethanone, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 1-(2,3,8,8-tetramethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-2-yl)ethan-1-one and / or isobornyl acetate; Other ingredients (e.g., amber, powdery spicy, or watery): dodecahydro-3a,6,6,9a-tetramethyl-naphtho[2,1-b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane, and / or 3-(3-isopropyl-1-phenyl)butanal. It may be.

[0043] In certain embodiments, the perfume raw material is capable of completely dissolving the 2-(alkylsulfonyl)octan-4-one compound according to formula (I) at 25°C.

[0044] In certain embodiments, the oil phase consists of perfume raw materials.

[0045] In certain embodiments, the oil phase comprises more than one perfume raw material, for example, the oil phase comprises from 2 to 50 perfume raw materials, or from 2 to 20 perfume raw materials, or from 2 to 10 perfume raw materials.

[0046] In a preferred embodiment, the perfume raw material is selected from the group of lactones.

[0047] In a preferred embodiment, the perfume raw material comprises a lactone, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof. Preferably, the perfume raw material is selected from the group consisting of lactones, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate (Hedione®), and mixtures thereof.

[0048] In a preferred embodiment, the perfume raw material comprises methyl 2-(3-oxo-2-pentylcyclopentyl)acetate (Hedione®), oct-2-en-4-one, gamma-lactone, delta-lactone, or any mixture thereof. Preferably, the gamma-lactone is gamma-nonalactone, gamma-decalactone, gamma-undecalactone, or gamma-valerolactone. Preferably, the delta-lactone is delta-nonalactone.

[0049] In a preferred embodiment, the perfume raw material is selected from the group consisting of methyl 2-(3-oxo-2-pentylcyclopentyl)acetate (Hedione®), oct-2-en-4-one, gamma-lactone, delta-lactone, and mixtures thereof. Preferably, the gamma-lactone is gamma-nonalactone, gamma-decalactone, gamma-undecalactone, or gamma-valerolactone. Preferably, the delta-lactone is delta-nonalactone.

[0050] In a particular embodiment, the perfume raw material is methyl 2-(3-oxo-2-pentylcyclopentyl)acetate (Hedione®).

[0051] In a particular embodiment, the perfume raw material is oct-2-en-4-one. In view of the ability of the compound of formula (I) to release oct-2-en-4-one, the embodiment can impart a particularly strong strawberry aroma. The oct-2-en-4-one can be in the form of its (E)- or (Z)-isomer, or a mixture thereof. Preferably, the oct-2-en-4-one is predominantly in the form of its (E)-isomer, with a minor amount of the (Z)-form, and even more preferably, the oct-2-en-4-one is in the form of its (E)-isomer.

[0052] In certain embodiments, the perfume raw material is gamma-lactone.

[0053] In certain embodiments, the perfume raw material is gamma-valerolactone.

[0054] In certain embodiments, the perfume raw material is gamma-nonalactone.

[0055] In certain embodiments, the perfume raw material is gamma-decalactone.

[0056] In certain embodiments, the perfume raw material is gamma-undecalactone.

[0057] In certain embodiments, the perfume raw material is a delta-lactone.

[0058] In certain embodiments, the perfume raw material is delta-nonalactone.

[0059] In certain embodiments, the perfume composition comprises at least 5% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0060] In certain embodiments, the perfume composition comprises at least 10% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0061] In certain embodiments, the perfume composition comprises at least 15% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0062] In certain embodiments, the perfume composition comprises at least 20% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0063] In certain embodiments, the perfume composition comprises at least 25% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0064] In certain embodiments, the perfume composition comprises at least 30% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0065] In certain embodiments, the perfume composition comprises at most 95% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0066] In certain embodiments, the perfume composition comprises at most 90% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0067] In certain embodiments, the perfume composition comprises at most 85% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0068] In certain embodiments, the perfume composition comprises at most 80% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0069] In certain embodiments, the perfume composition comprises at most 75% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0070] In certain embodiments, the perfume composition comprises at most 70% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.

[0071] In certain embodiments, the perfume raw materials are liquid at 25°C.

[0072] In a preferred embodiment, the perfume raw material is an essential oil.

[0073] In another embodiment, the oil phase comprises at least one perfume raw material that is an essential oil and at least one perfume raw material that is not an essential oil.

[0074] In certain embodiments, the essential oil is selected from the group consisting of eucalyptus oil, orange oil, and patchouli oil.

[0075] In certain embodiments, the oil phase comprises more than one essential oil, for example, the oil phase comprises 2 to 50 oils, or 2 to 20 oils, or 2 to 10 oils.

[0076] In certain embodiments, the perfume composition comprises essential oil in an amount of 95% by weight or less, hi some embodiments, the perfume composition comprises oil in an amount of 90% by weight or less, 80% by weight or less, 70% by weight or less, 60% by weight or less, or 50% by weight or less.

[0077] In certain embodiments, the perfume composition comprises perfume raw materials in an amount of 95% by weight or less, hi some embodiments, the perfume composition comprises perfume raw materials in an amount of 90% by weight or less, 80% by weight or less, 70% by weight or less, 60% by weight or less, or 50% by weight or less.

[0078] In certain embodiments, the perfume composition comprises perfume raw materials in an amount of 50 to 95% by weight, such as 60 to 95% by weight, or 70 to 95% by weight, or 80 to 95% by weight, or 85 to 95% by weight.

[0079] In certain embodiments, the oil phase further comprises a liquid carrier.

[0080] In certain embodiments, the liquid carrier is selected from the group consisting of diethyl phthalate, dimethyl glutarate, dimethyl adipate, ethyl oleate, dipropylene glycol (DIPG), DIPG methyl ether acetate, DIPG monomethyl ether, DIPG monoethyl ether, DIPG n-propyl ether, heptyl undecylenate, isocetyl alcohol, neopentyl glycol diethylhexanoate, isopropyl myristate (IPM), triacetin, dioctyl adipate, butoxypropanol, benzyl benzoate, benzyl alcohol, medium chain triglycerides, isopropylideneglycerol, ethyl lactate, diethylene glycol methyl ether, triethyl acetate, castor oil, 3-methoxy-3-methylbutanol, tripropylene glycol methyl ether, propylene glycol methyl ether, hexylene glycol, pentylene glycol, butylene glycol, 1,3-butanediol, 2,3-butanediol, 2-methylbutanol, n-propanol, iso-propanol, ethanol, propylene glycol, 1,3-propanediol, glycerol, n-alkanes and iso-alkanes.

[0081] In certain embodiments, the liquid carrier may be one or more of a group of alkanes, such as undecane or tridecane.

[0082] In certain embodiments, the oil phase comprises a lactone and a liquid carrier selected from the group of an IPM and an alkane.

[0083] In certain embodiments, the oil phase does not contain more than 50% by weight of liquid carrier, preferably more than 20% by weight, and more preferably more than 10% by weight.

[0084] In certain embodiments, the oil phase does not contain more than 50% by weight of dipropylene glycol (DIPG), preferably more than 20% by weight, and more preferably more than 10% by weight.

[0085] In certain embodiments, the oil phase is selected from the group consisting of diethyl phthalate, dimethyl glutarate, dimethyl adipate, ethyl oleate, dipropylene glycol (DIPG), DIPG methyl ether acetate, DIPG monomethyl ether, DIPG monoethyl ether, DIPG n-propyl ether, heptyl undecylenate, isocetyl alcohol, neopentyl glycol diethylhexanoate, isopropyl myristate (IPM), triacetin, dioctyl adipate, butoxypropanol, benzyl benzoate, benzyl alcohol, medium chain triglycerides, isopropylideneglycerol, ethyl lactate, diethylene glycol methyl ether, triethyl acetate, castor oil, 3-methoxy-3-methylbutanol, tripropylene glycol methyl ether, propylene glycol methyl ether, hexylene glycol, pentylene glycol, butylene glycol, 1,3-butanediol, 2,3-butanediol, 2-methylbutanol, n-propanol, iso-propanol, ethanol, propylene glycol, 1,3-propanediol, glycerol, n-alkanes, and iso-alkanes.

[0086] In certain embodiments, the oil phase does not include dipropylene glycol (DIPG).

[0087] In certain embodiments, the oil phase does not include isopropyl myristate (IPM).

[0088] In certain embodiments, the oil phase does not include triethyl citrate.

[0089] According to the invention, the perfuming composition comprises a compound of formula (I) in an amount of at least 5% by weight.

[0090] The present inventors have surprisingly found that it is difficult to find an oil phase capable of completely dissolving the compound of formula (I) at high concentrations at 25°C (room temperature). In particular, it has been found difficult to find a solvent / liquid carrier capable of completely dissolving the compound of formula (I) in an amount of at least 5% by weight and suitable for use in fragrance compositions. The requirement that the solvent be suitable for fragrance compositions significantly limits the range of solvents potentially useful for dissolving the compound of formula (I). For example, some solvents cannot be used for regulatory reasons or because they have strong chemical odors that are incompatible with fragrance manufacturing applications. Specifically, 2-methyl-tetrahydrofuran may be considered a good solvent for the compound of formula (I), but it is not suitable for fragrance compositions in view of its regulatory status.

[0091] The claimed levels of the compound of formula (I) in the perfume composition are beneficial in that they allow a significant effect to be achieved by the compound of formula (I) when the perfume composition is added to a consumer product. In this regard, the inventors have found that solvents commonly used for the preparation of perfume compositions are not very suitable for completely dissolving the compound of formula (I) at the claimed concentrations, but rather, surprisingly, perfume raw materials are found to be suitable for dissolving the compound of formula (I) at high concentrations at 25°C.

[0092] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of 5 to 50% by weight, preferably 5 to 20% by weight, more preferably 5 to 15% by weight.

[0093] In certain embodiments, the compound of formula (I) is present in the perfuming composition in an amount of at least 5% by weight.

[0094] In certain embodiments, the compound of formula (I) is present in the perfuming composition in an amount of at least 10% by weight.

[0095] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 15% by weight.

[0096] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 20% by weight.

[0097] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 25% by weight.

[0098] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 30% by weight.

[0099] In certain embodiments, the perfume composition further comprises a perfumery adjuvant.

[0100] By "perfuming adjuvant" is meant an ingredient capable of imparting additional benefits such as color, specific lightfastness, chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in perfumery compositions cannot be exhaustive, and it must be stated that said ingredients are well known to those skilled in the art. However, specific, non-limiting examples include viscosity agents (e.g., surfactants, thickeners, gelling and / or rheology modifiers), stabilizers (e.g., preservatives, antioxidants, heat / light and / or buffering agents or chelating agents, e.g., BHT), colorants (e.g., dyes and / or pigments), preservatives (e.g., antibacterial or antimicrobial or antifungal or anti-irritant agents), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins, and mixtures thereof.

[0101] In another aspect, the present invention provides a method for producing a perfume composition according to the present invention, comprising adding to an oil phase comprising at least one perfume raw material a compound of formula [ka] The method relates to a method comprising the step of dissolving a 2-(alkylsulfonyl)octan-4-one compound of the formula:

[0102] In certain embodiments, the 2-(alkylsulfonyl)octan-4-one compound of formula (I) is completely dissolved in the oil phase at a temperature of 25°C.

[0103] The embodiments and modifications described above with respect to the perfuming composition according to the invention also apply to the method according to the invention.

[0104] Another aspect of the present invention is a compound of formula [ka] The present invention relates to the use of at least one perfume raw material for dissolving a 2-(alkylsulfonyl)octan-4-one compound of the formula (I).

[0105] In certain embodiments, the 2-(alkylsulfonyl)octan-4-one compound of formula (I) is dissolved in the perfume raw materials and / or oils at a concentration of at least 5% by weight.

[0106] In certain embodiments, the 2-(alkylsulfonyl)octan-4-one compound of Formula (I) is completely dissolved at a temperature of 25°C.

[0107] In certain embodiments, the 2-(alkylsulfonyl)octan-4-one compound of formula (I) is present in a perfuming composition.

[0108] The perfuming compositions of the present invention can be advantageously used in all areas of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of consumer products to which said compositions are added.

[0109] Therefore, another aspect of the present invention relates to a consumer product comprising a perfuming composition according to the present invention.

[0110] For the sake of clarity, it is stated that the term "consumer product" is to be understood as a consumer product that is expected to deliver at least a pleasant perfuming effect to the surface to which it is applied (e.g., skin, hair, textiles, or hard surfaces). For the sake of clarity, the consumer product is a non-edible product.

[0111] Here, the nature and type of constituents of the perfumed consumer product do not warrant a more detailed description (which would in any case not be exhaustive), and a person skilled in the art can select them on the basis of his general knowledge and according to the nature and desired effect of this product.

[0112] Non-limiting examples of suitable consumer products include fragrances such as fine fragrances, splashes or eau de parfum, colognes or shave or aftershave lotions; fabric care products such as liquid, pod or solid detergents, optionally in pod or tablet form, fabric softeners, liquid or solid scent boosters, dryer sheets, fabric refreshers, ironing water, paper, bleach, carpet cleaners, curtain care products; body care products such as hair care products (e.g. shampoos, leave-on or rinse-off hair conditioners, coloring preparations or hairsprays, color care products, hair styling products), dental care products, disinfectants, intimate care products; cosmetic preparations (e.g. skin creams or lotions, vanishing creams or deodorants or or skin care products (e.g. soap, shower or bath mousse, oil or gel, or hygiene or foot / hand care products); air care products such as air fresheners or "ready to use" powdered air fresheners that can be used in residential spaces (rooms, refrigerators, cupboards, shoes or cars) and / or public spaces (hall, hotel, mall, etc.); or home care products such as mould removers, furniture care products, wipes, dish detergents or hard surface (e.g. floor, bathroom, hygiene or window cleaning) cleaners; leather care products; car care products such as polishes, waxes or plastic cleaners.

[0113] In certain embodiments, the consumer product is a personal or home care product, preferably a fabric conditioner, a solid or liquid detergent, a hard surface cleaner, a shampoo, a shower gel, a leave-on conditioner, or a rinse-off conditioner.

[0114] In certain embodiments, the consumer product has an acidic pH value, preferably below 5.5, preferably between 2.5 and 5.5.

[0115] The proportions at which the perfuming composition according to the invention can be incorporated into the various aforementioned articles or compositions can vary within wide ranges of values, these values ​​depending on the nature of the article or product to be perfumed.

[0116] In certain embodiments, the consumer product comprises the perfuming composition in an amount of 0.1 to 10% by weight, preferably 0.2 to 5% by weight, more preferably 0.3 to 4% by weight, and even more preferably 0.4 to 3% by weight, based on the total weight of the consumer product.

[0117] In certain embodiments, the consumer product comprises the perfume composition in an amount of less than 1% by weight.

[0118] In certain embodiments, the consumer product comprises greater than 2% by weight of the perfume composition.

[0119] In certain embodiments, the consumer product comprises the perfume composition in an amount less than 1% by weight or more than 2% by weight.

[0120] In certain embodiments, the consumer product comprises the perfuming composition in an amount of from 0.1% to less than 1% by weight.

[0121] In certain embodiments, the consumer product comprises the perfuming composition in an amount greater than 2% to 10% by weight.

[0122] In certain embodiments, the consumer product is a fragrance, a fabric care product, a body care product, a cosmetic preparation, a skin care product, an air care product, or a home care product. Preferably, the consumer product is a fabric softener, a shower gel, or a rinse-off hair conditioner.

[0123] According to certain embodiments of the present invention, the scented consumer product of the present invention is a liquid fabric softener comprising a fabric softener active base in an amount comprised between 85 and 100% by weight based on the total weight of the scented consumer product. The fabric softener active base may comprise dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts, Hamburg ester quats, triethanolamine quats, silicones, and mixtures thereof.

[0124] According to a specific embodiment of the present invention, the consumer product of the present invention is an all-purpose cleaner comprising an all-purpose cleaner active base in an amount of 85-100% by weight based on the total weight of the consumer product. The all-purpose active base may comprise a linear alkylbenzene sulfonate (LAS) in an amount of 0-4%, preferably 1-2%, a nonionic surfactant in an amount of 0-8%, preferably 2-4%, and an acid such as citric acid in an amount of 0.1-0.5%.

[0125] According to a particular embodiment of the present invention, the scented consumer product of the present invention is a shampoo or shower gel comprising a shampoo or shower gel active base in an amount comprised between 85 and 100% by weight based on the total weight of the scented consumer product. The shampoo or shower gel active base may comprise sodium alkyl ether sulfate, ammonium alkyl ether sulfate, alkyl amphoacetate, cocamidopropyl betaine, cocamide MEA, alkyl polyglucoside, and an amino acid-based surfactant.

[0126] According to a particular embodiment of the present invention, the scented consumer product of the present invention is a bar soap comprising a soap active base in an amount comprised between 85 and 100% by weight based on the total weight of the scented consumer product. The bar soap active base may comprise a salt of a weak acid, typically a fatty acid, and a strong base, such as sodium hydroxide.

[0127] According to a particular embodiment of the present invention, the scented consumer product of the present invention is a rinse-off conditioner comprising a rinse-off conditioner active base in an amount comprised between 85 and 99.95% by weight based on the total weight of the scented consumer product. The rinse-off conditioner active base may comprise cetyltrimonium chloride, stearyltrimonium chloride, benzalkonium chloride, behentrimonium chloride, and mixtures thereof.

[0128] According to a specific embodiment of the present invention, the consumer product of the present invention is a liquid detergent comprising a liquid detergent active base in an amount of 85 to 100% by weight based on the total weight of the consumer product. The liquid detergent active base may comprise an anionic surfactant such as alkyl benzene sulfonate (ABS), linear alkyl benzene sulfonate (LAS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), sodium lauryl ether sulfate (SLES), or methyl ester sulfonate (MES); a nonionic surfactant such as alkylamine, alkanolamide, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymer, amine oxide, alkyl polyglucoside, or alkyl polyglucosamide; or a mixture thereof.

[0129] According to a specific embodiment of the present invention, the consumer product of the present invention is a solid detergent comprising a solid detergent active base in an amount of 85 to 100% by weight based on the total weight of the consumer product. The solid detergent active base may comprise at least one surfactant selected from the group consisting of anionic, nonionic, cationic, zwitterionic surfactants, and mixtures thereof. The surfactant in the solid detergent active base is preferably selected from the group consisting of linear alkene benzene sulfonic acid (LABS), sodium laureth sulfate, sodium lauryl ether sulfate (SLES), sodium lauryl sulfate (SLS), alpha olefin sulfonate (AOS), methyl ester sulfonate (MES), alkyl polyglycoside (APG), primary alcohol ethoxylate, particularly lauryl alcohol ethoxylate (LAE), primary alcohol sulfonate (PAS), soap, and mixtures thereof. The solid detergent active base may comprise further components commonly used in powder detergent consumer products selected from the group consisting of bleaching agents such as EDTA (tetraacetylethylenediamine); buffering agents; builders such as zeolites, sodium carbonate or mixtures thereof; soil-releasing or soil-suspending polymers; granular enzyme particles such as cellulase, lipase, protease, mannanase, pectinase or mixtures thereof; corrosion inhibitors; antifoaming agents; dyes; fillers such as sodium silicate, sodium sulfate or mixtures thereof; a source of hydrogen peroxide such as sodium percarbonate or sodium perborate; and mixtures thereof.

[0130] In certain embodiments, the consumer product comprises a preservative preferably selected from the group consisting of benzisothiazolin-3-one, methylchloroisothiazolinone, methylisothiazolinone, and any mixture thereof.

[0131] The present invention also relates to the use of a perfuming composition according to the invention for the manufacture of a consumer product.

[0132] Example Solubility measurements: Solid 2-(dodecylsulfonyl)octan-4-one was mixed with different solvents and transferred to 8 mL vials equipped with an overhead stirrer. The samples were placed in a Crystalline PV instrument (Technobis, The Netherlands). Heating and cooling steps were applied under mechanical stirring, and the samples were monitored by tracking the transparency via an LED light beam passing through the vial. Complete (100%) transparency is achieved when 2-(dodecylsulfonyl)octan-4-one is completely dissolved in the solvent. On the other hand, when the transparency reading is below 100%, the dissolution process is still incomplete.

[0133] Determination of solubilization temperature: The first heating step was performed by rapidly heating the sample (+5°C / min) above its dissolution temperature to 60°C. After complete dissolution, a cooling gradient (-2°C / min) was applied to 1°C, i.e., below the sample's dissolution temperature, where the sample was stirred until 2-(dodecylsulfonyl)octan-4-one crystallized. The second heating step was then performed by applying a shallow heating gradient (+0.1°C / min) to dissolve the material under quasi-isothermal conditions. The sample's transparency was monitored as a function of time during the heating gradient. The dissolution process was completed when the signal reached 100% transparency, and the respective temperature was considered the solubilization temperature (T_sol).

[0134] Solubilization temperature of 5% by weight of 2-(dodecylsulfonyl)octan-4-one in different solvents / fragrance raw materials Following the methodology described above, 2-(dodecylsulfonyl)octan-4-one was mixed at a concentration of 5% by weight with various solvents / liquid carriers or perfume raw materials suitable for perfume manufacturing compositions, and the solubilization temperatures were determined. The solvents and perfume raw materials used, along with their respective solubilization temperatures, are shown in Tables 1-3 below.

[0135] [Table 1]

[0136] [Table 2]

[0137] [Table 3]

[0138] The fragrance compositions shown in Table 2 were as follows: [Table 4]

[0139] [Table 5]

[0140] [Table 6]

[0141] [Table 7]

[0142] [Table 8]

[0143] From Tables 1 to 3 above, it can be observed that the oil phase containing the perfume raw material and the perfume raw material mixture was able to completely dissolve 2-(dodecylsulfonyl)octan-4-one at a concentration level of 5% by weight at 25° C. However, typical solvents used in perfume manufacturing (such as ethyl lactate, dimethyl glutarate, isopropyl myristate, triethyl citrate, triacetin, dipropylene glycol, and Cetiol® Ultimate) were unable to completely dissolve 2-(dodecylsulfonyl)octan-4-one at a concentration level of 5% by weight at 25° C. alone, since complete dissolution of 2-(dodecylsulfonyl)octan-4-one could only be achieved for these solvents at temperatures higher than 25° C.

[0144] temperature solubility curve Following the methodology described above, 2-(dodecylsulfonyl)octan-4-one was mixed at different concentrations with various solvents or perfume raw materials and the solubilization temperature was determined.

[0145] [Table 9]

[0146] Soluble amounts of 2-(dodecylsulfonyl)octan-4-one in different solvents / fragrance raw materials at 25°C: The solubility of 2-(dodecylsulfonyl)octan-4-one in various solvents or perfume raw materials at 25°C was determined based on the data shown in Table 9. For each solvent or perfume raw material, the measured solubility as a function of temperature was fitted with an exponential function. The solubility at 25°C was obtained by extrapolating or interpolating this exponential function. The results / exponential curves are shown in Figure 1 (black triangles: DIPG, grey squares: IPM, open diamonds: Hedione®, black circles: gamma-nonalactone and Cetiol® Ultimate (80 / 20); the solid line represents the exponential fit to the experimental data).

[0147] [Table 10]

[0148] [Table 11]

[0149] From Tables 10 and 11, it can be observed that the oil phases containing gamma-nonalactone and Cetiol® Ultimate (80 / 20; v / v), and Hedione®, respectively, were able to completely dissolve large amounts of 2-(dodecylsulfonyl)octan-4-one (more than 5% by weight). However, the common solvents isopropyl myristate and dipropylene glycol were unable to completely dissolve large amounts of 2-(dodecylsulfonyl)octan-4-one at 25°C. Only amounts less than 3% by weight could be dissolved by these solvents at 25°C.

Claims

1. A fragrance composition comprising: - of the following formula (I) 【Chemical 1】 wherein n is an integer between 1 and 9. and a 2-(alkylsulfonyl)octan-4-one compound of the formula: an oil phase comprising at least one perfume raw material; Including, The compound of formula (I) is present in the fragrance composition in an amount of at least 5% by weight. Perfume composition.

2. 2. The perfume composition according to claim 1, wherein the compound of formula (I) is completely dissolved in the oil phase at a temperature of 25°C.

3. 3. The perfume composition according to claim 1, wherein the perfume raw material is selected from the group consisting of fragrance oils, essential oils, or combinations thereof.

4. A perfuming composition according to any one of claims 1 to 3, wherein n is an integer between 3 and 7, preferably between 4 and 6, more preferably n is 5.

5. A perfuming composition according to any one of claims 1 to 4, consisting of the compound of formula (I) and the oil phase.

6. 6. The fragrance composition according to claim 1, wherein the compound of formula (I) is present in the fragrance composition in an amount of 5 to 50% by weight, preferably 5 to 20% by weight, more preferably 5 to 15% by weight.

7. 7. The perfume composition according to claim 1, wherein the oil phase comprises at least one perfume raw material.

8. 7. The perfuming composition according to claim 1, wherein the oil phase further comprises a solvent.

9. 9. The perfume composition according to claim 1, wherein the perfume raw material comprises a lactone, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof, preferably wherein the perfume raw material is selected from the group consisting of lactone, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, and a mixture thereof.

10. 10. The fragrance composition according to claim 1, wherein the fragrance raw material is selected from the group consisting of methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, oct-2-en-4-one, gamma-lactone, delta-lactone, and mixtures thereof.

11. 11. The perfuming composition according to claim 1, wherein the oil phase is free of a liquid carrier.

12. 12. A perfuming composition according to any one of claims 1 to 11, wherein the oil phase does not contain more than 50% by weight of dipropylene glycol (DIPG), preferably more than 20% by weight, more preferably more than 10% by weight.

13. A method for producing a perfume composition according to any one of claims 1 to 12, comprising adding an ester of a compound represented by the following formula (I) to an oil phase containing at least one perfume raw material: 【Chemistry 2】 2. The method of claim 1, wherein the compound is a 2-(alkylsulfonyl)octan-4-one compound of formula (I).

14. The following formula (I) 【Chemistry 3】 Use of at least one perfume raw material for dissolving a 2-(alkylsulfonyl)octan-4-one compound of formula (I) above.

15. A consumer product comprising a perfuming composition according to any one of claims 1 to 12.

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