Perfuming compositions comprising 2-(alkylsulfonyl) octan-4-one
By mixing the 2-(alkylsulfonyl)octyl-4-one compound with the oil of the fragrance raw material and containing at least 5% by weight of the compound in the fragrance composition, the problem in the prior art is solved that it is difficult to completely dissolve the compound at room temperature, and the effect of efficient dissolution and enhancement of the fragrance durability and olfactory impact is achieved.
Patent Information
- Application Number
- CN202380071204.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2022-10-07
- Filing Date
- 2023-10-05
- Publication Date
- 2025-05-16
AI Technical Summary
The prior art is difficult to completely dissolve high concentrations of 2-(alkylsulfonyl)octyl-4-one compounds at room temperature, resulting in a dilution effect when used in fragrance compositions, affecting the durability of the fragrance and the olfactory impact.
By mixing the 2-(alkylsulfonyl)octyl-4-one compound with the oil of the fragrance feed, it is ensured that at least 5% by weight of the compound is contained in the fragrance composition and the compound is completely dissolved at 25°C using the solubility of the fragrance feed.
It realizes efficient dissolution of high concentrations of 2-(alkylsulfonyl)octyl-4-one compounds at room temperature, enhancing the fragrance durability and olfactory impact of the aroma composition, and meeting consumers' demand for long-lasting red berry flavors.
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Figure CN120018836A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a perfuming 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 the perfuming composition in an amount of at least 5% by weight. The present invention also relates to a method for preparing the perfuming composition and a consumer product comprising the perfuming composition. Background Art
[0002] Consumers usually associate the efficacy of perfumed products with the long-lastingness or substantivity of the perfume (perfume). Perfumes consist of a variety of compounds with different volatilities, which are applied to the surface and then evaporate from the surface to be smelled. Perfumes are applied to surfaces, such as hard surfaces, fabrics, skin or hair, by perfumed compositions or perfumed consumer products (such as high-quality fragrances (fine fragrances) or various detergents and cleaning agents). Due to the high volatility of the aromatics that make up the perfume, the odor emitted from the perfumed surface can only be perceived for a limited time. In particular, the so-called top notes of perfume evaporate quite quickly. They are the most volatile compounds in the composition and represent the freshness of the perfume. Top notes usually include citrus, floral, green and fruity notes, etc., especially fruity notes are deeply loved by consumers. Several types of fruity notes are used in perfumes, an example of which is the fragrance of red berries, such as raspberries or strawberries. Oct-2-en-4-one can be used as a perfume ingredient to provide a natural strawberry scent when used in perfume compositions or perfumed consumer products. However, this compound is very volatile so that its scent imparted to surfaces such as hard surfaces, fabrics, skin or hair lasts only for a relatively short period of time.
[0003] Consumers seek fragrances that are stable in the target application and at the same time long-lasting and / or submissive, being smelled hours or even days after application. In particular, long-lasting red berry notes, such as strawberry, are ideal.
[0004] To this end, fragrance precursors such as 2-(alkylsulfonyl)octan-4-one compounds can be used, which can slowly generate oct-2-en-4-one over time, thereby providing a long-lasting strawberry smell to the environment (see WO 2019 / 243369).
[0005] 2-(Alkylsulfonyl)octan-4-one compounds can be advantageously used in perfuming compositions, such as fragrance oils. However, such compounds do not always dissolve easily in fragrance oils. For example, 2-(dodecylsulfonyl)octan-4-one is solid at room temperature, so the handling of this compound is different from that of typical perfume raw materials. One option is to melt the compound above its melting point (49-51°C) before mixing with the fragrance oil; however, once the temperature drops below the melting point, 2-(dodecylsulfonyl)octan-4-one tends to resolidify rapidly. Another option is to mix solid 2-(alkyldodecylsulfonyl)octan-4-one directly with the fragrance oil, which requires effective stirring and / or heating to achieve uniform mixing and complete dissolution.
[0006] In order to overcome the above problems, the 2-(alkylsulfonyl)octan-4-one compound may be provided in the form of a solution, that is, the 2-(alkylsulfonyl)octan-4-one compound may be dissolved in a solvent.
[0007] However, when the 2-(alkylsulfonyl)octan-4-one compound is first dissolved in a solvent and then added to the perfuming composition, the compound is provided in a diluted form, which inevitably reduces the amount of said compound added. In order 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. In order to ensure that the 2-(alkylsulfonyl)octan-4-one compound has a sufficiently high olfactory impact (initial effectiveness) in the final application, the perfuming 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 it is not easy to provide a solvent system that meets the above requirements. In particular, the inventors of the present invention have found that solvents commonly used in the art for dissolving fragrances and fragrance precursors, such as dipropylene glycol (DIPG) or isopropyl myristate (IPM), cannot fully dissolve the required concentration of 2-(alkylsulfonyl)octan-4-one compounds at room temperature. Therefore, the object of the present invention is to find a solvent that can dissolve a large amount of 2-(alkylsulfonyl)octan-4-one compounds at room temperature to ensure that an olfactory sufficient amount of 2-(alkylsulfonyl)octan-4-one compounds can be used in the perfuming composition. BRIEF DESCRIPTION OF THE DRAWINGS
[0009] The solubility of 2-(dodecylsulfonyl)octan-4-one in different liquid carriers and oil phases varies with
[0010] Temperature changes. Black triangles: DIPG, gray squares: IPM, open diamonds: Black circles: γ-nonalactone and Ultimate(80 / 20). The continuous line represents the exponential function fitted to the experimental data. Summary of the invention
[0011] The present invention relates to a perfuming composition comprising:
[0012] - a 2-(alkylsulfonyl)octan-4-one compound of formula (I),
[0013]
[0014] Where n is an integer from 1 to 9;
[0015] - an oily phase comprising at least one fragrance raw material;
[0016] Thereby, the compound of formula (I) is present in the perfuming composition in an amount of at least 5% by weight.
[0017] Another aspect of the invention relates to a process for preparing a perfuming composition according to the 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.
[0018] The present invention also relates to the use of at least one fragrance raw material for dissolving a 2-(alkylsulfonyl)octan-4-one compound of formula (I).
[0019] Furthermore, the invention relates to a consumer product comprising a perfuming composition according to the invention. DETAILED DESCRIPTION
[0020] The present invention relates to a perfuming composition comprising:
[0021] - a 2-(alkylsulfonyl)octan-4-one compound of formula (I),
[0022]
[0023] Where n is an integer from 1 to 9;
[0024] - an oily phase comprising at least one fragrance raw material;
[0025] Thereby, the compound of formula (I) is present in the perfuming composition in an amount of at least 5% by weight.
[0026] By "oil phase" is meant an ingredient or composition which is liquid at about 20°C and which is immiscible or only miscible to a small extent with the aqueous phase.
[0027] In a particular embodiment, the perfuming composition consists of a compound of formula (I) and an oily phase.
[0028] According to the invention, the perfuming composition comprises a 2-(alkylsulfonyl)octan-4-one compound of formula (I).
[0029] The compounds according to formula (I) can act as fragrance precursor compounds, as they can slowly generate oct-2-en-4-one over time, thereby providing a persistent strawberry smell to the environment. The expression "strawberry smell" or "strawberry note" is understood as an odor reminiscent of strawberry fruit.
[0030] The compounds according to formula (I) are themselves non-volatile and are substantially odourless. The formation of oct-2-en-4-one from the compounds of formula (I) may be triggered by one or more of the following triggers: the presence of moisture / oxygen, changes in pH, the presence of enzymes and elevated temperature.
[0031] According to the present invention, the integer n in formula (I) is 1 to 9.
[0032] In one specific embodiment, n is 1. In another embodiment, n is 2. In another embodiment, n is 3. In another embodiment, n is 4. In another embodiment, n is 5. In another embodiment, n is 6. In another embodiment, n is 7. In another embodiment, n is 8. In another embodiment, n is 9.
[0033] In a preferred embodiment, the integer n is from 3 to 7. Preferably, the integer n is from 4 to 6. More preferably, n is 5. When n is 5, the compound of formula (I) is 2-(dodecylsulfonyl)octan-4-one. Therefore, in a preferred embodiment, the compound of formula (I) is 2-(dodecylsulfonyl)octan-4-one.
[0034] In a particular embodiment, the perfuming composition comprises more than one compound according to formula (I).
[0035] In one embodiment, the perfuming composition comprises from 1 to 5 compounds of formula (I).
[0036] In one embodiment, the perfuming composition comprises one compound of formula (I).
[0037] In one embodiment, the perfuming composition comprises two compounds of formula (I).
[0038] In one embodiment, the perfuming composition comprises three compounds of formula (I).
[0039] In one embodiment, the perfuming composition comprises four compounds of formula (I).
[0040] In one embodiment, the perfuming composition comprises five compounds of formula (I).
[0041] According to the invention, the perfuming composition comprises an oily phase comprising at least one perfume raw material.
[0042] In a preferred embodiment, the compound of formula (I) is fully dissolved in the oil phase at a temperature of 25° C. Therefore, in the preferred embodiment, the oil phase is able to fully dissolve the compound of formula (I) at a temperature of 25° C.
[0043] The skilled person is well aware of suitable means of 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. If 100% light transparency 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. Therefore, in a specific embodiment, the complete dissolution of the compound of formula (I) is determined based on complete light transparency at 25°C. For this measurement, the dissolved sample can be present in a glass vial.
[0044] The term "solubility at 25°C" is intended to mean the thermodynamic equilibrium solubility of the compound of formula (I) at 25°C. It is well known to those skilled in the art that the solubility of any solid compound can increase significantly with the increase in the temperature of the solvent system. Subsequently, even if the temperature returns to a lower temperature, such as 25°C, the solid compound can remain in the solution for a period of time in a supersaturated state. However, this is an apparent solubility due to non-equilibrium, metastable state and limited shelf life stability, and therefore must be distinguished from the thermodynamic solubility at equilibrium. For example, the thermodynamic solubility can be determined at a controlled temperature using the so-called shake flask method. Alternatively, it can be determined by slowly heating the compound and recording the dissolution temperature after complete dissolution.
[0045] In a particular embodiment, the oil phase is capable of completely dissolving the compound of formula (I).
[0046] In a particular embodiment, the oil phase consists of at least one fragrance raw material.
[0047] In a specific embodiment, the perfuming composition comprises the oily phase in an amount of 95% by weight or less. In an embodiment, the perfuming composition comprises the oily 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.
[0048] In a particular embodiment, the perfuming composition comprises the oil phase in an amount ranging from 50 to 95% by weight, for example from 60 to 95% by weight, or from 70 to 95% by weight, or from 80 to 95% by weight, or from 85 to 95% by weight.
[0049] According to the invention, the oil phase comprises fragrance raw materials.
[0050] A "fragrance compound" or "fragrance raw material (PRM)" is a compound that is used as an active ingredient in a perfuming composition to impart a hedonic effect. In other words, to be considered a fragrance compound, the compound must be recognized by those skilled in the art of perfumery as being able to impart or modify the odor of a composition in an active or pleasant manner, rather than merely possessing an odor.
[0051] The nature and types of perfume raw materials present in the perfuming composition of the invention do not warrant a more detailed description here, which is in no way exhaustive, and a person skilled in the art will be able to choose them according to his general knowledge and according to the intended use or application and the desired organoleptic effect. In general, these perfume raw materials belong to different chemical classes, such as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogen- or sulfur-containing heterocyclic compounds and essential oils, and may be of natural or synthetic origin.
[0052] Many of these flavoring ingredients are listed in references, for example in the book Perfume and Flavor Chemicals, 1969, Montclair, NJ, USA, by S. Arctander, or its latest editions, or in other works of a similar nature, such as Fenaroli's Handbook of Flavor Ingredients, 1975, CRC Press or MB Jacobs' Synthetic Food Adjuncts, 1947, van Nostrand Co., Inc., as well as in the extensive patent literature in the field of perfumery.
[0053] Fragrance raw materials may be, for example:
[0054] Aldehyde fragrance ingredients: (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-carboxaldehyde, 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-n-propyl)benzaldehyde, 4-methylbenzaldehyde, 2-methylpropionic acid 4-formyl-2-methoxyphenyl ester, (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;
[0055] Aromatic herbal ingredients: camphor, eucalyptol, 5-methyltricyclo[6.2.1.0~2,7~]undec-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4-dimethyl-1,3-oxathiacyclohexane, 2,2,7 / 8,9 / 10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and / or α-pinene;
[0056] Balsamic ingredients: coumarin, ethyl vanillin and / or vanillin;
[0057] Citrus aroma ingredients: dihydromyrcenol, citral, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and / or 1,4(8)-p-menthenadiene;
[0058] Floral fragrance ingredients: methyl dihydrojasmonate, linalool, citronellol, phenylethyl alcohol, 3-(4-tert-butylphenyl)-2-methylpropanal, hexyl cinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, β-ionone (β-violet ketone), methyl 2-(methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, (1E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1- Penten-3-one, 1-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, (2E)-1-[2,6,6-trimethyl-3-cyclohexen-1-yl]-2-buten-1-one, (2E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one, 2,5-dimethyl-2-indanemethanol, 2,6,6-trimethyl-3-cyclohexene -1-formate, 3-(4,4-dimethyl-1-cyclohexen-1-yl) propanal, hexyl salicylate, 3,7-dimethyl-1,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2-methylpropanal, tricyclodecenyl acetate, geraniol, p-menth-1-en-8-ol, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, 1,1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, methyl homocis-dihydrojasmonate, 3-methyl-5-phenyl-1-pentanol , tricyclodecenyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-menthol, (S)-2-(1,1-dimethylpropoxy)propyl propionate, 2-methoxynaphthalene, 2,2,2-trichloro-1-phenylethyl acetate, 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamaldehyde, 8-decene-5-lactone, 4-phenyl-2-butanone, isononyl acetate, 4-(1,1-dimethylethyl)-1-cyclohexyl acetate, tricyclodecenyl isobutyrate, and / or a mixture of methylionone isomers;
[0059] Fruity ingredients: γ-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1,3-oxathiacyclohexane, 4-decanoic acid, 2-methyl-ethyl valerate, hexyl acetate, 2-methylbutyric acid ethyl ester, γ-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, 2-methyl-1,3-dioxolane-2-ethyl acetate, 3-(3,3 / 1,1-dimethyl-5-indanyl) propanal, Diethyl 1,4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3-dimethylcyclohexyl]ethyl [3-ethyl-2-oxiranyl]acetate, 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;
[0060] Green fragrance ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styroyl acetate, (2-methylbutoxy) allyl acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and / or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one;
[0061] Musk ingredients: 1,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecan-1-one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecene-2-one, 1-oxa-13-cyclohexadecene-2-one, (9Z)-9-cycloheptadecene-1-one, 2-{1S)-1-[(1R)-3,3-dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3-methyl-5-cyclohexane Pentadecene-1-one, 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-g-2-benzopyran, (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate, oxacyclohexadecane-2-one and / or (1S,1'R)-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl propionate;
[0062] Wood fragrance 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[2,9'-tricyclo[6.2.1.0 2,7] undec[4]ene, (1-ethoxyethoxy)cyclododecane, 2,2,9,11-tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone, (1'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-butene- 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;
[0063] Other ingredients (e.g., amber, powdery, spicy, or watery): dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan and any of its stereoisomers, piperonal, anisaldehyde, eugenol, cinnamaldehyde, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 7-methyl-2H-1,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl-1,2,3,4,4a,5,6,7-octahydro-2-naphthol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro[4.4]nonane, and / or 3-(3-isopropyl-1-phenyl)butanal.
[0064] In a particular embodiment, the fragrance raw material is fully soluble in the 2-(alkylsulfonyl)octan-4-one compound according to formula (I) at 25°C.
[0065] In a particular embodiment, the oil phase consists of fragrance raw materials.
[0066] In a particular embodiment, the oil phase comprises more than one perfume raw material, for example, the oil phase comprises 2 to 50 perfume raw materials, or 2 to 20 perfume raw materials, or 2 to 10 perfume raw materials.
[0067] In a preferred embodiment, the fragrance raw materials are selected from lactones.
[0068] In a preferred embodiment, the fragrance raw material comprises lactone, 2-(3-oxo-2-pentylcyclopentyl)acetic acid methyl ester, or a mixture thereof. Preferably, the fragrance raw material is composed of lactone, 2-(3-oxo-2-pentylcyclopentyl)acetic acid methyl ester. and mixtures thereof.
[0069] In a preferred embodiment, the fragrance raw material comprises methyl 2-(3-oxo-2-pentylcyclopentyl)acetate Oct-2-en-4-one, γ-lactone, δ-lactone, or any mixture thereof. Preferably, the γ-lactone is γ-nonalactone, γ-decanoic acid, γ-undecalactone or γ-valerolactone. Preferably, the δ-lactone is δ-nonalactone.
[0070] In a preferred embodiment, the fragrance raw material is prepared from methyl 2-(3-oxo-2-pentylcyclopentyl)acetate. The ester is selected from the group consisting of oct-2-en-4-one, γ-lactone, δ-lactone, and mixtures thereof. Preferably, the γ-lactone is γ-nonalactone, γ-decanoic acid, γ-undecalactone or γ-valerolactone. Preferably, the δ-lactone is δ-nonalactone.
[0071] In a particular embodiment, the fragrance raw material is methyl 2-(3-oxo-2-pentylcyclopentyl)acetate
[0072] In a specific embodiment, the fragrance raw material is oct-2-ene-4-one. In view of the potential of the compound of formula (I) to release oct-2-ene-4-one, the embodiment is particularly capable of providing a strong strawberry smell. Oct-2-ene-4-one can be in the form of its (E)- or (Z)-isomer, or a mixture thereof. Preferably, oct-2-ene-4-one is mainly in the form of its (E)-isomer, containing a small amount of (Z)-form, and even more preferably, oct-2-ene-4-one is in the form of its (E)-isomer.
[0073] In a particular embodiment, the fragrance raw material is a gamma-lactone.
[0074] In a particular embodiment, the fragrance raw material is gamma-valerolactone.
[0075] In a particular embodiment, the fragrance raw material is gamma-nonalactone.
[0076] In a particular embodiment, the fragrance raw material is gamma-decanolide.
[0077] In a particular embodiment, the fragrance raw material is gamma-undecalactone.
[0078] In a particular embodiment, the fragrance raw material is a delta-lactone.
[0079] In a particular embodiment, the fragrance raw material is delta-nonalactone.
[0080] In a particular embodiment, the perfuming composition comprises at least 5% by weight of lactones, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0081] In a particular embodiment, the perfuming composition comprises at least 10% by weight of lactones, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0082] In a particular embodiment, the perfuming composition comprises at least 15% by weight of lactones, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0083] In a particular embodiment, the perfuming composition comprises at least 20% by weight of lactones, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0084] In a particular embodiment, the perfuming composition comprises at least 25% by weight of lactones, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0085] In a particular embodiment, the perfuming composition comprises at least 30% by weight of lactones, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0086] In a particular embodiment, the perfuming composition comprises up to 95% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0087] In a particular embodiment, the perfuming composition comprises up to 90% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0088] In a particular embodiment, the perfuming composition comprises up to 85% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0089] In a particular embodiment, the perfuming composition comprises up to 80% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0090] In a particular embodiment, the perfuming composition comprises up to 75% by weight of lactone, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0091] In a particular embodiment, the perfuming composition comprises up to 70% by weight of lactones, oct-2-en-4-one, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or mixtures thereof.
[0092] In a particular embodiment, the fragrance raw material is liquid at 25°C.
[0093] In a preferred embodiment, the fragrance raw material is an essential oil.
[0094] In another embodiment, the oil phase comprises at least one fragrance raw material that is an essential oil and at least one fragrance raw material that is not an essential oil.
[0095] In a specific embodiment, the essential oil is selected from the group consisting of eucalyptus oil, orange oil and patchouli oil.
[0096] In a particular embodiment, 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.
[0097] In a particular embodiment, the perfuming composition comprises essential oils in an amount of 95% by weight or less. In an embodiment, the perfuming composition comprises oils 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.
[0098] In a particular embodiment, the perfuming composition comprises the perfume raw materials in an amount of 95% by weight or less. In an embodiment, the perfuming composition comprises the 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.
[0099] In a particular embodiment, the perfuming 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.
[0100] In a particular embodiment, the oil phase further comprises a liquid carrier.
[0101] In a specific embodiment, the liquid carrier can be 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, isohexadecanol, neopentyl glycol diethylhexanoate, isopropyl myristate (IPM), triacetin, dioctyl adipate, butoxypropanol, benzyl benzoate, benzyl alcohol, medium chain triglycerides, isopropyl glycerol, 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. glycol), 1,3-butanediol, 2,3-butanediol, 2-methylbutanol, n-propanol, isopropanol, ethanol, 1,2-propylene glycol (propylene glycol), 1,3-propanediol, glycerol, normal alkanes and isoalkanes.
[0102] In a particular embodiment, the liquid carrier may be one or more of the group of alkanes, such as undecane or tridecane.
[0103] In a particular embodiment, the oil phase comprises a lactone and a liquid carrier selected from the group of an IPM and an alkane.
[0104] In a particular embodiment, the oil phase does not comprise more than 50% by weight of liquid carrier, preferably does not exceed 20% by weight, more preferably does not exceed 10% by weight.
[0105] In a particular embodiment, the oil phase does not contain more than 50 wt.-% dipropylene glycol (DIPG), preferably not more than 20 wt.-%, more preferably not more than 10 wt.-%.
[0106] In a specific embodiment, the oil phase does not contain one or more liquid carriers 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, isohexadecanol, neopentyl glycol diethylhexanoate, isopropyl myristate (IPM), triacetin, hexyl glycerol, Dioctyl bis(octyl styrene glycol), butoxypropanol, benzyl benzoate, benzyl alcohol, medium chain triglycerides, isopropyl glycerol, 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-butylene glycol, 2,3-butylene glycol, 2-methylbutanol, n-propanol, isopropanol, ethanol, 1,2-propylene glycol, 1,3-propylene glycol, glycerol, n-alkanes and iso-alkanes.
[0107] In a specific embodiment, the oil phase does not contain dipropylene glycol (DIPG).
[0108] In a particular embodiment, the oil phase does not comprise isopropyl myristate (IPM).
[0109] In a specific embodiment, the oil phase does not comprise triethyl citrate.
[0110] According to the invention, the perfuming composition comprises the compound of formula (I) in an amount of at least 5% by weight.
[0111] The inventors of the present invention have surprisingly found that it is difficult to find an oil phase that can fully dissolve a high concentration of the compound of formula (I) at 25°C (room temperature). In particular, it has been found that it is difficult to find a solvent / liquid carrier that can fully dissolve an amount of at least 5% by weight of the compound of formula (I) and is suitable for use in a perfume composition. The requirement that the solvent needs to be suitable for a perfume composition significantly limits the range of potentially useful solvents for dissolving the compound of formula (I). For example, certain solvents cannot be used for regulatory reasons or because they have a strong chemical odor that is incompatible with perfumery applications. In particular, 2-methyl-tetrahydrofuran can be considered a good solvent for the compound of formula (I), but in view of its regulatory status, it is not suitable for use in perfume compositions.
[0112] The claimed content of the compound of formula (I) in the perfuming composition is advantageous in ensuring that the compound of formula (I) is able to exert a significant effect when the perfuming composition is added to a consumer product. In this regard, the inventors have found that the solvents commonly used to prepare perfuming compositions are not well suited to fully dissolve the compound of formula (I) at the claimed concentrations, whereas surprisingly, perfume raw materials are suitable for dissolving the compound of formula (I) at high concentrations at 25°C.
[0113] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount ranging from 5 to 50% by weight, preferably from 5 to 20% by weight, more preferably from 5 to 15% by weight.
[0114] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 5% by weight.
[0115] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 10% by weight.
[0116] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 15% by weight.
[0117] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 20% by weight.
[0118] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 25% by weight.
[0119] In a particular embodiment, the compound of formula (I) is present in the perfuming composition in an amount of at least 30% by weight.
[0120] In a particular embodiment, the perfuming composition further comprises a perfume adjuvant.
[0121] By "perfume adjuvants" it is meant here ingredients capable of imparting additional added benefits, such as colour, specific lightfastness, chemical stability, etc. A detailed description of the nature and types of adjuvants commonly used in perfuming compositions cannot be exhaustive, but it must be mentioned that said ingredients are well known to the person skilled in the art. The following may be cited as specific non-limiting examples: viscosity agents (e.g. surfactants, thickeners, gelling agents and / or rheology modifiers), stabilizers (e.g. preservatives, antioxidants, heat / light and / or buffers or chelating agents, such as BHT), colourants (e.g. dyes and / or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungal or anti-irritant), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins and mixtures thereof.
[0122] In another aspect, the invention relates to a process for preparing a perfuming composition according to the invention, comprising the steps of dissolving a 2-(alkylsulfonyl)octan-4-one compound of formula (I) in an oil phase comprising at least one perfume raw material,
[0123]
[0124] In a particular embodiment, the 2-(alkylsulfonyl)octan-4-one compound of formula (I) is completely dissolved in the oil phase at a temperature of 25°C.
[0125] The embodiments and modifications given above for the perfuming composition according to the invention apply equally to the method according to the invention.
[0126] Another aspect of the present invention relates to the use of at least one fragrance raw material for dissolving a 2-(alkylsulfonyl)octan-4-one compound of formula (I),
[0127]
[0128] In a particular embodiment, the 2-(alkylsulfonyl)octan-4-one compound of formula (I) is dissolved in the fragrance raw material and / or oil at a concentration of at least 5% by weight.
[0129] In a particular embodiment, the 2-(alkylsulfonyl)octan-4-one compound of formula (I) is completely soluble at a temperature of 25°C.
[0130] In a particular embodiment, the 2-(alkylsulfonyl)octan-4-one compound of formula (I) is present in the perfuming composition.
[0131] The perfuming composition of the invention can be advantageously used in all areas of modern perfumery, ie fine perfumery or functional perfumery, to actively impart or modify the odor of a consumer product to which it is added.
[0132] Therefore, another aspect of the invention relates to a consumer product comprising a perfuming composition according to the invention.
[0133] For the sake of clarity, it is mentioned that the term "consumer product" is to be understood as a consumer product intended to deliver at least one pleasant perfuming effect to a surface to which it is applied, such as skin, hair, fabric or hard surface. For the sake of clarity, a consumer product is a non-edible product.
[0134] The nature and types of ingredients of perfumed consumer products do not warrant a more detailed description here, which is in no way exhaustive, the skilled person being able to choose them on the basis of his general knowledge and according to the characteristics of the product in question and the desired effect.
[0135] Non-limiting examples of suitable perfumed consumer products include perfumes, such as fine perfumes, splashes or eau de perfumes, colognes or shaving lotions or aftershaves; fabric care products, such as liquid or solid detergents, fabric softeners, liquid or solid fragrance enhancers, 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, dyeing preparations or hair sprays, color care products, hair styling products, dental care products), disinfectants, intimate care products; cosmetic preparations (e.g. skin creams or lotions, vanishing creams or body deodorants (deodorants) or antiperspirants (e.g. sprays or roll-ons)), depilatories, tanning products, sunscreen or aftersun products, beauty products. nail products, skin cleansers, cosmetics); or skin care products (e.g. soaps, shower or bath mousses, bath oils or shower gels, or hygiene products or foot / hand care products); air care products, such as air fresheners or "ready-to-use" powder air fresheners, which can be used in domestic spaces (rooms, refrigerators, cupboards, shoes or cars) and / or public spaces (lobbies, hotels, shopping malls, etc.); or home care products, such as mildew removers, furniture care agents, wipes, dishwashing detergents or detergents for hard surfaces (e.g. floors, bathrooms, sanitary ware or window cleaning); leather care products; car care products, such as polishes, waxes or plastic cleaners.
[0136] In a particular embodiment, the consumer product is a personal care product or a home care product, preferably a fabric conditioner, a solid or liquid detergent, a hard surface cleaner, a shampoo, a body wash, a leave-on conditioner, or a rinse-off conditioner.
[0137] In a particular embodiment, the consumable product has an acidic pH, preferably a pH below 5.5, preferably a pH between 2.5 and 5.5.
[0138] The proportions in which the perfuming composition according to the invention can be incorporated into the various preparations or compositions mentioned above vary within wide ranges of values. These values depend on the nature of the objects or products to be perfumed.
[0139] In a particular embodiment, the consumer product comprises the perfuming composition in an amount of 0.1 to 10 wt.-%, preferably 0.2 to 5 wt.-%, more preferably 0.3 to 4 wt.-%, even more preferably 0.4 to 3 wt.-%, based on the total weight of the consumer product.
[0140] In a particular embodiment, the consumer product comprises the perfuming composition in an amount of less than 1% by weight.
[0141] In a particular embodiment, the consumer product comprises the perfuming composition in an amount higher than 2% by weight.
[0142] In a particular embodiment, the consumer product comprises the perfuming composition in an amount of less than 1% by weight or higher than 2% by weight.
[0143] In a particular embodiment, the consumer product comprises the perfuming composition in an amount of 0.1 % to less than 1 % by weight.
[0144] In a particular embodiment, the consumer product comprises the perfuming composition in an amount of greater than 2% to 10% by weight.
[0145] In a particular embodiment, the consumer product is a perfume, 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.
[0146] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a liquid fabric softener comprising a fabric softener active base in an amount of 85 to 100% by weight, based on the total weight of the perfumed consumer product. The fabric softener active base may comprise dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts, Hamburg ester quaternary ammonium salts (esterquat), triethanolamine quaternary ammonium salts, silicones and mixtures thereof.
[0147] According to a particular embodiment of the invention, the consumer product of the invention is a multi-purpose cleaner comprising a multi-purpose cleaner active base in an amount of 85 to 100% by weight, based on the total weight of the perfumed consumer product. The multi-purpose active base may comprise linear alkylbenzene sulfonate (LAS) in an amount of 0 to 4%, preferably 1 to 2%, a nonionic surfactant in an amount of 0 to 8%, preferably 2 to 4%, and an acid, such as citric acid, in an amount of 0.1 to 0.5%.
[0148] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a shampoo or shower gel comprising a shampoo or shower gel active base in an amount of 85 to 100% by weight, based on the total weight of the perfumed 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 glucosides and amino acid-based surfactants.
[0149] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a soap bar comprising a soap active base in an amount ranging from 85 to 100% by weight, based on the total weight of the perfumed consumer product. The soap bar active base may comprise a salt of a weak acid, typically a salt of a weak acid (which may be a fatty acid) and a strong base such as sodium hydroxide.
[0150] According to a particular embodiment of the invention, the perfumed consumer product of the invention is a rinse-off conditioner comprising a rinse-off conditioner active base in an amount of 85 to 99.95 wt.-%, based on the total weight of the perfumed consumer product. The rinse-off conditioner active base may comprise cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, benzalkonium chloride, behenyltrimethylammonium chloride and mixtures thereof.
[0151] According to a particular 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 perfumed consumer product. The liquid detergent active base may comprise anionic surfactants such as alkylbenzene sulfonates (ABS), linear alkylbenzene sulfonates (LAS), secondary alkyl sulfonates (SAS), primary alcohol sulfates (PAS), lauryl ether sulfates (LES), sodium lauryl ether sulfate (SLES), methyl ester sulfonates (MES); nonionic surfactants such as alkylamines, alkanolamides, fatty alcohol poly(ethylene glycol) ethers, fatty alcohol ethoxylates (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxides, alkyl polyglucosides, alkyl polyglucamides; or mixtures thereof.
[0152] According to a particular embodiment of the invention, the consumer product of the 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 perfumed 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 olefin benzene sulfonates (LABS), sodium laureth sulfate, sodium lauryl ether sulfate (SLES), sodium lauryl sulfate (SLS), alpha-olefin sulfonates (AOS), methyl ester sulfonates (MES), alkyl polyglucosides (APG), primary alcohol ethoxylates, in particular lauryl alcohol ethoxylate (LAE), primary alcohol sulfonates (PAS), soaps and mixtures thereof. The solid detergent active base may contain additional ingredients commonly used in powdered detergent consumer products, selected from the group consisting of: bleaching agents such as TAED (tetraacetylethylenediamine); buffering agents; builders, such as zeolite, sodium carbonate or mixtures thereof; soil release agents or soil suspension polymers; granular enzyme particles, such as cellulase, lipase, protease, mannanase, pectinase or mixtures thereof; corrosion inhibitors; defoamers; suds suppressors; dyes; fillers, such as sodium silicate, sodium sulfate or mixtures thereof; sources of hydrogen peroxide, such as sodium percarbonate or sodium perborate; and mixtures thereof.
[0153] In a particular embodiment, the consumable product comprises a preservative, preferably selected from the group consisting of benzisothiazolin-3-one, methylchloroisothiazolinone, methylisothiazolinone, and any mixture thereof.
[0154] The invention also relates to the use of a perfuming composition according to the invention for the preparation of a consumer product.
[0155] Example
[0156] Solubility Measurements:
[0157] Solid 2-(dodecylsulfonyl)octan-4-one was mixed with different solvents and then transferred to an 8 mL vial equipped with an overhead stirrer. The sample was placed in a Crystalline PV instrument (Technobis, The Netherlands). The heating and cooling steps were performed under mechanical stirring, and the sample was monitored by tracking the transparency through an LED beam passing through the vial. When 2-(dodecylsulfonyl)octan-4-one was completely dissolved in the solvent, complete (100%) transparency was achieved. On the other hand, when the measured transparency value was less than 100%, the dissolution process was still incomplete.
[0158] Determination of melting temperature:
[0159] The first heating step is to quickly (+5°C / min) heat the sample to above its dissolution temperature, i.e. to 60°C. After complete dissolution, the gradient is cooled to 1°C (-2°C / min), i.e. below the dissolution temperature of the sample, while the sample is stirred until 2-(dodecylsulfonyl)octan-4-one crystallizes. The second heating step is then carried out using a slow gradient heating (+0.1°C / min) so that the material is dissolved under quasi-isothermal conditions. During the gradient heating process, the transparency of the sample is monitored over time. Once the signal reaches 100% transparency, the dissolution process is terminated and the respective temperature is taken as the dissolution temperature (T_sol).
[0160] Dissolution temperature of 5 wt% 2-(dodecylsulfonyl)octan-4-one in different solvents / fragrance raw materials
[0161] According to the method described above, 2-(dodecylsulfonyl)octan-4-one was mixed with various solvents / liquid carriers suitable for perfume compositions or with perfume raw materials at a concentration of 5% by weight, and the dissolution temperature was determined. The solvents and perfume raw materials used and their respective dissolution temperatures are listed in Tables 1 to 3 below.
[0162] Table 1. Dissolution temperatures of 5 wt% 2-(dodecylsulfonyl)octan-4-one in various fragrance raw materials.
[0163]
[0164] Ultimate: A mixture of undecane and tridecane
[0165] Methyl 2-(3-oxo-2-pentylcyclopentyl)acetate
[0166] Table 2. Dissolution temperatures of 5 wt% 2-(dodecylsulfonyl)octan-4-one in different fragrance compositions.
[0167]
[0168] Table 3. Dissolution temperatures of 5 wt% 2-(dodecylsulfonyl)octan-4-one in various solvents / liquid carriers compatible with fragrance applications.
[0169]
[0170] The fragrance compositions given in Table 2 are as follows:
[0171] Table 4: Composition of fragrance composition F1
[0172]
[0173] 2-Isobutyl-4-methyltetrahydro-2H-pyran-4-ol
[0174] 2-(1-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropyl propionate 3 Iso ESuper: 1-(octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone (mixture of isomers)
[0175] Oxyheterocyclic hexadec-12- and / or 13-en-2-one
[0176] 3-Methyl-4- or 5-cyclopentadecen-1-one (E / Z isomer mixture)
[0177] Table 5: Composition of fragrance composition F2
[0178]
[0179] 1 Coranol: 4-cyclohexyl-2-methylbutan-2-ol
[0180] 1-(3,3- or 5,5-dimethylcyclohex-1-en-1-yl)pent-4-en-1-one
[0181] 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1-b]furan
[0182] Oxahedraloxane-2-one
[0183] Table 6: Composition of fragrance composition F3
[0184]
[0185] Table 7: Composition of fragrance composition F4
[0186]
[0187] Table 8: Composition of fragrance composition F5
[0188]
[0189] 1 Manzanate: 2-Methylvalerate Ethyl Ester
[0190] Cyclohexane-1,4-dicarboxylic acid diethyl ester
[0191] As can be seen from Tables 1 to 3 above, the oil phase containing the fragrance raw materials and the fragrance raw material mixture is able to completely dissolve 2-(dodecylsulfonyl)octan-4-one at a concentration level of 5 wt% at 25°C. However, typical solvents used in the fragrance industry (e.g., ethyl lactate, dimethyl glutarate, isopropyl myristate, triethyl citrate, triacetin, dipropylene glycol and Ultimate) itself cannot completely dissolve 2-(dodecylsulfonyl)octan-4-one at a concentration level of 5 wt% at 25°C, because these solvents can completely dissolve 2-(dodecylsulfonyl)octan-4-one only at temperatures above 25°C.
[0192] Temperature Solubility Curve
[0193] According to the method described above, 2-(dodecylsulfonyl)octan-4-one was mixed with various solvents or fragrance raw materials at different concentrations and the dissolution temperature was determined.
[0194] Table 9. Dissolution temperatures of 2-(dodecylsulfonyl)octan-4-one at various concentrations in different solvents / fragrance raw materials.
[0195]
[0196] Soluble amount of 2-(dodecylsulfonyl)octan-4-one in different solvents / fragrance raw materials at 25°C:
[0197] Based on the data presented in Table 9, the solubility of 2-(dodecylsulfonyl)octan-4-one in various solvents or fragrance raw materials at 25°C was determined. For each solvent or fragrance raw material, the measured solubility versus temperature has been fitted to an exponential function. The solubility at 25°C was obtained by extrapolation or interpolation of the exponential function. The results / exponential curves are shown in the figure (black triangles: DIPG, gray squares: IPM, open diamonds: Black circles: γ-nonalactone and Ultimate (80 / 20). The continuous line represents the exponential function fitted to the experimental data).
[0198] Table 10. Total soluble amount of 2-(dodecylsulfonyl)octan-4-one in fragrance raw materials at 25°C obtained from temperature-solubility curves.
[0199]
[0200] Table 11. Total soluble amount of 2-(dodecylsulfonyl)octan-4-one in DIPG and IPM at 25°C obtained from temperature-solubility curves.
[0201]
[0202] It can be seen from Tables 10 and 11 that the compositions of the present invention respectively contain γ-nonalactone and Ultimate (80 / 20; v / v) and The oil phase can completely dissolve a high content of 2-(dodecylsulfonyl)octan-4-one (content greater than 5 wt%). However, the commonly used solvents isopropyl myristate and dipropylene glycol cannot completely dissolve a high content of 2-(dodecylsulfonyl)octan-4-one at 25° C. These solvents can only dissolve less than 3 wt% at 25° C.
Claims
1. A perfuming composition comprising: - a 2-(alkylsulfonyl)octan-4-one compound of formula (I), Where n is an integer from 1 to 9; - an oily phase comprising at least one fragrance raw material; in, The compound of formula (I) is present in the perfuming composition in an amount of at least 5% by weight.
2. A perfuming composition according to claim 1, wherein the compound of formula (I) is completely soluble in the oil phase at a temperature of 25°C.
3. The perfuming composition according to claim 1 or 2, wherein the fragrance 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 from 3 to 7, preferably from 4 to 6, more preferably n is 5.
5. Perfuming composition according to any one of claims 1 to 4, wherein the perfuming composition consists of a compound of formula (I) and the oily phase.
6. A perfuming composition according to any one of claims 1 to 5, wherein the compound of formula (I) is present in the perfuming composition in an amount ranging from 5 to 50% by weight, preferably from 5 to 20% by weight, more preferably from 5 to 15% by weight.
7. Perfuming composition according to any one of claims 1 to 6, wherein the oil phase consists of at least one perfume raw material.
8. Perfuming composition according to any one of claims 1 to 6, wherein the oil phase also comprises a solvent.
9. The perfuming composition according to any one of claims 1 to 8, wherein the perfume raw material comprises lactone, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof, preferably the perfume raw material is selected from the group consisting of lactone, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, or a mixture thereof.
10. A perfuming composition according to any one of claims 1 to 9, wherein the perfume 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. Perfuming composition according to any one of claims 1 to 10, wherein the oil phase does not comprise a liquid carrier.
12. Perfuming composition according to any one of claims 1 to 11, wherein the oily phase does not contain more than 50% by weight of dipropylene glycol (DIPG), preferably not more than 20% by weight, more preferably not more than 10% by weight.
13. Process for preparing a perfuming composition as claimed in any one of the preceding claims, 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, 14. Use of at least one fragrance raw material for dissolving a 2-(alkylsulfonyl)octan-4-one compound of formula (I), 15. A consumer product comprising the perfuming composition of any one of claims 1 to 12.
Citation Information
Patent Citations
Compounds for providing a long-lasting strawberry odor
WO2019243369A1