Improvements in or relating to organic compounds

Abstract

This disclosure relates to methods of making perfume oils comprising difficult to solubilize absolutes, by separating the perfume ingredients into first and second functional parts, wherein the first part comprises the absolutes and a polar solvent having a ClogP of 1.5 or less. The disclosure also relates to perfume oils made in accordance with the method.

Description

[0001] Improvements in or relating to organic compounds

[0002] This disclosure relates to perfume oils, consumer products containing said oils, and methods of manufacturing them.

[0003] BACKGROUND OF THE INVENTION

[0004] The manufacture of perfumed consumer products involves preparing perfume oils that can be stably incorporated into said products. Such perfume oils are obtained by mixing together a number of ingredients that are carefully chosen for their hedonic or functional properties. A perfume oil may comprise tens or even hundreds of ingredients, with widely varying physical and chemical properties. Indeed, a perfume oil may contain ingredients that are not (or are only partially) compatible with each other, leading to solubility issues. For example, some ingredients may not dissolve completely in the oil as a whole or may dissolve only to precipitate thereafter during a period of storage. This can be particularly problematic in the case of natural solid or semisolid absolutes, such as resinoids and butters, and crystalline ingredients, such as vanillin, ethyl vanillin, coumarin, evernyl, maltol, and ethyl maltol. During the last decades, these solubility issues have been typically solved by adding large amounts of solvents to the oil.

[0005] In recent times within the field of perfumery, there has been an emphasis on using solvents more sparingly in the creation of perfume oils, and where possible using (in some cases, less efficient) natural and renewable solvents in preference to the petrochemical kind. At the same time, consumer trends, in particular but not exclusively, for powerful gourmand and oriental perfumes has seen the increased use of difficult to solubilize absolutes, such as benzoin, Myrrh or Tonka resinoids. These competing factors have combined to create new solubility challenges in perfume oil manufacture. Compatibility issues, such as the appearance of turbidity or the formation of precipitates in perfume oils, creates constraints on perfumers, forcing them to either limit the use of hedonically useful, yet problematic ingredients or to use excessive amounts of solvents, frustrating the drive for both interesting new hedonics and more natural and renewable perfumes. There is a need to provide perfume oils that incorporate in a stable way difficult to solubilize ingredients at levels that enable perfumers to create innovative hedonic effects, whilst containing relatively low levels of the solvents needed to solubilize them. There is also a need to provide methods that resolve compatibility issues caused by the use of these difficult to solubilize ingredients in perfume oils whilst minimizing the required amount of solvents needed to fulfil this task.SUMMARY OF THE INVENTION

[0006] In a first aspect, the invention provides a perfume oil comprising, based on the total weight of the perfume oil:

[0007] 0.2 to 20 wt.% of at least one absolute;

[0008] 0 to 30 wt.% of a Group Al perfume ingredient;

[0009] 0 to 30 wt.% of a Group A2 perfume ingredient;

[0010] 2 to 20 wt % of at least one polar solvent having a ClogP of 1.5 or less;

[0011] 20 to 80 wt.% of at least one Group B perfume ingredient;

[0012] wherein a Group Al perfume ingredient is solid at 25 °C and has a ClogP of 3.0 or less; a Group A2 perfume ingredient is liquid at 25 °C and has a ClogP of 3.0 or less; a Group B ingredient has a ClogP that is greater than 3.0 and is not an absolute; wherein the sum of the concentrations of the at least one absolute, the Group Al and Group A2 perfume ingredients is from 5 to 60 wt.%; and wherein the ratio of the sum of the concentration of the at least one absolute and Group Al ingredients to the concentration of the at least one polar solvent is from 0.2 to 5.

[0013] In a second aspect, the invention provides a perfume oil according to the first aspect of the invention in a form in which the perfume oil comprises separate but functionally interacting first and second parts, wherein the first part comprises the absolute, optionally Group Al ingredients, polar solvent and optionally Group A2 ingredients; the ratio of the sum of the concentration of absolute and Group Al ingredients to the concentration of the at least one polar solvent is from 0.2 to 5; and the second part comprises the Group B ingredients.

[0014] In a third aspect, the invention provides a method of manufacturing a perfume oil according to the first or second aspects of the invention, the method comprising the steps of

[0015] - Providing first and second parts, wherein the first part comprises the absolute, optionally Group Al perfume ingredients, the polar solvent and optionally Group A2 perfume ingredients and the ratio of the sum of the concentration of the absolute and Al perfume ingredients to the polar solvent is from 0.2 to 5; and the second part comprises the Group B ingredients;

[0016] - Dissolving the absolute and optionally Group Al ingredients in the first part; and

[0017] - Blending the first part in which absolute optionally Group Al ingredients are dissolved with the second part to form the perfume oil.

[0018] In a fourth aspect, the invention provides the use of a mixture of at least one polar solvent having a ClogP of 1.5 or less and optionally a Group A2 perfume ingredient for solubilizing absolutes andoptionally Group Al ingredients, wherein the weight ratio of the sum of absolutes and Group Al ingredients to the polar solvent is from 0.2 to 5.

[0019] In a fifth aspect, the invention provides a consumer product comprising a perfume oil according to the first and second aspects of the invention.

[0020] The details, examples and preferences provided in relation to any one or more of the stated aspects or embodiments of the present invention will be further described herein and apply equally to all aspects and embodiments of the present invention. Any combination of embodiments, examples and preferences described herein in all possible variations thereof are encompassed by the present invention unless otherwise indicated herein, or otherwise clearly contradicted by context.

[0021] DEFINITIONS

[0022] By “perfumed product” is meant a composition comprising the perfume oil and a base, wherein the base comprises ingredients used in household, laundry or personal care products, such as surfactants and / or solvents.

[0023] By “perfume ingredient” is meant an ingredient that is primarily used for its olfactive character in a perfume oil. In the context of the present invention, the term “perfume ingredient” does not include solvents.

[0024] By “absolute” is meant a fragrant mixture that is obtained from natural sources (including plants, fungi, algae or animal sources) by extraction methods described below. An absolute is typically a solid or semi-solid at a temperature of 25 °C that comprises difficult to solubilise components, that may include sesquiterpenes, polyphenols, flavonoids and solid fatty acids. For the avoidance of doubt, although Group Al perfume ingredients are solids, they are not absolutes as this term is used in the present invention.

[0025] Absolutes are obtained from natural sources by extraction methods known in the art, including maceration, decoction, enfleurage, steam distillation, reflux extraction, supercritical CO2 extraction, percolation, ultrasound-assisted and microwave-assisted extraction, and pervaporation. By “solid or semi-solid” is meant a substance that is firm and stable in shape when submitted to gravitational forces. Such a substance may typically be crystalline, amorphous, resinous, pasteous, butter-like and / or waxy.

[0026] By “ClogP” is meant the calculated logarithm of the octanol / water partition coefficient P. The calculated logP is called clogP or ClogP, wherein the nomenclature ClogP is used for values calculated using the original calculation method developed at Pomona college, which have then been commercialized by BioByte, Inc. of Claremont, CA. and Daylight Chemical InformationSystems, Inc. of Aliso Viejo, CA. The ClogP calculation software implemented in Perkin-Elmer ChemDraw software provides ClogP values that are suitable for the sake of the present invention.

[0027] DETAILED DESCRIPTION OF THE INVENTION

[0028] In accordance with the first aspect of the invention, provided are perfume oils characterized by the surprisingly high levels of incorporation of difficult to solubilize absolutes and optionally also solid, more particularly crystalline solid perfume ingredients (so-called Group Al ingredients), using relatively little amounts of polar solvents to solubilize them. The invention therefore expands the creative tool box of perfumers, enabling them to utilize interesting natural absolutes and crystalline ingredients, without the concomitant disadvantage of using high levels of solvents to stably incorporate them into a perfume oil.

[0029] The invention is based on the surprising discovery that the task of dissolving the such difficult to solubilize ingredients could be significantly simplified when they are dissolved using at least one polar solvent having a ClogP of 1.5 or less, when the process of dissolving them is carried out in the absence of Group B perfume ingredients. The applicant also found in a surprising manner that dissolution could be further aided by dissolving the absolutes and optionally Group Al ingredients in said polar solvent optionally in the presence of a Group A2 perfume ingredient.

[0030] Any absolutes can be incorporated into a perfume oil according to the invention. However, in particular embodiments, the at least one absolute is selected from cistus absolute, hydrocarboresins, Myrrh resinoid, Oakwood absolute, Fir balsam, Bran absolute, Mate absolute, roasted Barley absolute, Benzoin resinoid, Akigala wood absolute, Bergamot absolute, Labdanum resinoid, Galbanum resinoid, Olibanol, Tonka bean absolute, roasted Tonka bean absolute, Orris butter, Cocoa absolute, and Coffee absolute.

[0031] In WO 2008 / 050086, a perfume recipe is disclosed that contains absolutes, polar solvents and ingredients that could be characterized as Al, A2 and B ingredients. In particular, in Example 2 of that document the recipe “C3” is disclosed that contains 3 wt % Bangalol ((E)-2-ethyl-4-(2,2,3-trimethyl-1 -cyclopent-3 -enyl)but-2-en-l-ol); 4 wt % Benzoin Siam Resinoid 50 % in DPG; 3 wt % Bergamot oil; 2 wt % Cis 3 Hexenol 10% in DPG; 1 wt % Coumarin; 3 wt % Dihydromyrcenol; 16 wt % Ethylene Brassylate (1, 4-dioxacy cl oheptadecane-5, 17-dione); 1 wt % Heliotropin (benzo[d][l,3]dioxole-5-carbaldehyde); 18 wt % Lavender oil; 5 wt % Lyral (4-(4-hydroxy-4-methylpentyl)cyclohex-3-enecarbaldehyde); 10 wt % Methyl dihydroj asm onate (methyl 3-oxo-2-pentylcyclopentaneacetate); 12 wt % methyl ionone alpha iso; 3 wt % Oak Moss Synthetic 10 % in DPG; 3 wt % Olibanum resinoid; 3 wt % Patchouli light oil; 6 wt % Prunella; 4 wt % Silvanone (16-Hexadecanolide); and 3 wt % Vanillin. This recipe is recited as a simple list of ingredientswithout any description of its method of preparation. Whereas, the manner in which the ingredients are combined, is not disclosed and there isn’t any description of the physical appearance or condition of the ingredients when mixed, the recipe C3 is disclaimed from the scope of the present invention.

[0032] In more particular embodiments the at least one absolute is selected from cistus absolute, hydrocarboresins, Myrrh resinoid, Oakwood absolute, Fir balsam, Bran absolute, Mate absolute, roasted Barley absolute, Akigala wood absolute, Bergamot absolute, Labdanum resinoid, Galbanum resinoid, Tonka bean absolute, roasted Tonka bean absolute, Orris butter, Cocoa absolute, and Coffee absolute.

[0033] In still more particular embodiments, the at least one absolute is selected from Tonka bean absolute, Cocoa absolute and Coffee absolute.

[0034] The at least one polar solvent that can be used to dissolve the difficult to solubilize ingredients may be selected from the group consisting of triethyl citrate, diethyl citrate, dipropylene glycol, propylene glycol, 1,3 -propanediol, 1,2-propanediol, 1,3 -butanediol, 1,2-butanediol, 1,2-pentanediol, ethanol, glycerol carbonate, isopropylidene glycerol and mixtures thereof.

[0035] Non-limiting examples of Group Al perfume ingredients that are particularly of use in the present invention are listed in Table 1.

[0036] Table 1. Examples of Group Al perfume ingredients

[0037] Al Ingredients ClogP 3-hydroxybutan-2-one (e.g. ACETOIN); -0.20 l-(4-methoxyphenyl)ethanone (e.g. ACETANISOLE); 1.80 1 -phenyl ethanone (e.g. ACETOPHENONE); 1.58 (E)-2-methoxy-4-(prop-l-en-l-yl)phenyl acetate (e.g. ACETYL ISOEUGENOL); 2.48 l-(2-pyrazinyl)ethanone (e.g. ACETYL PYRAZINE); -0.08 (lR,5S,E)-l,5-dimethylbicyclo[3.2.1]octan-8-one oxime (e.g. BUCCOXIME); 2.55 8-methyl-l,5-benzodioxepin-3-one (e.g. CALONE); 1.80 2-hydroxy-3-methylcyclopent-2-enone (e.g. CORYLONE); 0.42 2H-chromen-2-one (e.g. COUMARIN); 1.41 2-methoxy-4-methylphenol (e.g. CREOSOL); 1.82 p-cresol 1.97 1,4-dimethoxybenzene (e.g. DIMETHYL HYDROQUINONE); 2.15 2-ethyl-3-hydroxy-4H-pyran-4-one (e.g. ETHYL MALTOL); 0.63 3-ethoxy-4-hydroxybenzaldehyde (e.g. ETHYL VANILLIN); 1.81 methyl 2,4-dihydroxy-3,6-dimethylbenzoate (e.g. EVERNYL); 2.73 benzo[d][l,3]dioxole-5-carbaldehyde (e.g. HELIOTROPINE); 1.76

[0038]

[0039] 4-(l,3-benzodioxol-5-yl)butan-2-one (e g. HELIOTROPYL ACETONE); 1.534,4a,5,9b-tetrahydroindeno[l,2-d][l,3]dioxine (e.g. INDOFLOR); 1.41 IH-indole (e g. INDOLE); 2.13 3-hydroxy-2-methyl-4H-pyran-4-one (e.g. MALTOL); 0.10 l-(2-naphthalenyl)-ethanone (e.g. GRANGER CRYSTALS); 2.76 3-methoxy-5-methylphenol (e.g. ORCINYL3); 2.07 2-phenylacetic acid 1.41 4-(4-hydroxyphenyl)butan-2-one (e.g. Raspberry ketone); 1.22 2-ethoxy-4-methylphenol (e.g. ULTRAVANIL); 2.35 4-hydroxy-3 -methoxybenzaldehyde (e.g. VANILLIN); 1.28 benzoic acid 1.85 4-(l-3-benzodioxol-5-yl)-2-butanone (e.g. DULCINYL); 1.89

[0040]

[0041] Particularly preferred Group Al ingredients include but are not limited to vanillin, ethyl vanillin, coumarin, evemyl, heliotropin, maltol, ethyl maltol, and mixtures thereof.

[0042] Group A2 perfume ingredients may advantageously assist the solubilisation of the difficult to solubilize absolutes and Group Al ingredients. Moreover, the addition of these ingredients into the perfume oil may also prevent incompatibilities that might arise when mixing Group A2 ingredients and Group B ingredients.

[0043] Non-limiting examples of Group A2 perfume ingredients that are particularly of use in the present invention are listed in Table 2.

[0044] Table 2. Example of Group A2 perfume ingredients

[0045] A2 ingredients ClogP A2 ingredients ClogP allyl 2-phenoxyacetate (e.g. ACETATE

[0046] 2.45 (Z)-hex-3-en-l-yl acetate 2.34 PA)

[0047] N-ethyl-N-(m-tolyl)propionamide (e.g.

[0048] 2.66 (Z)-hex-3-en-l-yl formate 1.90 AGARBOIS)

[0049] 2-ethyl-4-hydroxy-5-methylfuran- hexan-l-ol (e g. ALCOHOL C 6) 1.88 3(2H)-one (e.g. 1.60 HOMOFURONOL)

[0050] octan-l-ol (e.g. ALCOHOL C 8 2-phenylpropanal (e.g.

[0051] 2.94 2.09 OCTYLIC) HYDRATROPIC ALDEHYDE)

[0052] 4-formyl-2-methoxyphenyl 2- hexanal (e.g. Aldehyde C 6 hexylic) 1.89 methylpropanoate (e.g. 1.72 ISOBUTAVAN)

[0053] 2-methylpropyl 3- methoxypyrazine (e.g.

[0054] heptanal (e g. ALDEHYDE C 7) 2.42 2.59 ISOBUTYL METHOXY PYRAZINE)

[0055] (E)-2-methoxy-4-(prop- 1 -en- 1 - octanal (e g. ALDEHYDE C 8) 2.95 2.58

[0056]

[0057] yl)phenol (e.g. ISOEUGENOL)5-methyl-2-(prop- 1 -en-2- pentyl formiate 1.85 yl)cyclohexanol (e.g. 2.75

[0058] ISOPULEGOL)

[0059] (Z)-6-(pent-2-en- 1 -yl)tetrahydro- l-octene-3-ol (e.g. AMYL VINYL

[0060] 2.43 2H-pyran-2-one (e.g. JASMIN 1.91 CARBINOL)

[0061] LACTONE DELTA)

[0062] (E)-6-(pent-3 -en- 1 -yl)tetrahy dro- 4-methoxybenzyl acetate (e.g. ANISYL

[0063] 1.88 2H-pyran-2-one (e.g. 1.91 ACETATE)

[0064] JASMOLACTONE)

[0065] 4-methoxybenzaldehyde (e.g. (Z)-hex-3-en-l-yl methyl

[0066] 1.78 2.26 ANISALDEHYDE) carbonate (e.g. LIFFAROME)

[0067] 2-(5-methyl-5- benzyl acetate 1.96 vinyltetrahydrofuran-2-yl)propan- 1.83

[0068] 2-ol (e.g. LINALOOL OXIDE)

[0069] 4-phenylbutan-2-one (e.g. BENZYL 3 , 7 -dimethylocta- 1 , 6-dien-3 -ol 1.89 2.75 ACETONE) (e.g. LINALOOL)

[0070] ethyl 6-acetoxyhexanoate (e.g. 2-(4-m ethylcyclohex-3 -en- 1 - 1.79 2.63 BERRYFLOR) yl)propan-2-ol (e.g. LINDENOL)

[0071] (4E)-9-hydroxy-5,9-dimethyl-4- butyl acetate 1.77 2.12 decenal (e.g. MAHONIAL)

[0072] 4-(4-methoxyphenyl)butan-2-one 2-methylpropyl acetate (e.g. BUTYL

[0073] 1.77 (e g. FRAMBINON METHYL 1.81 ACETATE, ISO)

[0074] ETHER)

[0075] methyl 2-(3-oxo-2- l-(p-tolyl)ethanone (e.g. pentylcyclopentyl)acetate (e.g. 2.91 2.08

[0076] METHYL ACETOPHENONE) CEPIONATE)

[0077] (E)-3-phenylprop-2-enenitrile (e.g. methyl 2-aminobenzoate (e.g.

[0078] 2.11 2.12 CINNAMALVA) METHYL ANTHRANILATE)

[0079] (E)-3-phenylprop-2-en-l-ol (e.g.

[0080] 1.61 methyl benzoate 2.11 CINNAMIC ALCOHOL)

[0081] (2E)-3-phenylprop-2-enal (e.g. methyl 3-phenylprop-2-enoate 2.05 2.46 CINNAMIC ALDEHYDE) (e.g. METHYL CINNAMATE)

[0082] (Z)-2-methyl-3- 2-(2-mercaptopropan-2-yl)-5- phenylacrylaldehyde (e.g. methylcyclohexanone (e.g. CORPS 2.51 2.36

[0083] METHYL CINNAMIC CASSIS)

[0084] ALDEHYDE)

[0085] 5-hexyl-5-methyloxolan-2-one

[0086] (4-methylphenyl) acetate (e.g. CRESYL

[0087] 1.99 (e g. METHYL DECALACTONE 2.88 ACETATE PARA)

[0088] GAMMA)

[0089] 2-ethoxy-4- l-methoxy-4-methylbenzene (e.g.

[0090] 2.56 (methoxymethyl)phenol (e.g. 1.65 CRESYL METHYL ETHER PARA)

[0091] METHYL DIANTILIS)

[0092] (Z)-m ethyl 2-(3 -oxo-2-(pent-2-en- 4-isopropylbenzaldehyde (e.g. CUMINIC

[0093] 2.92 l-yl)cyclopentyl)acetate (e.g. 2.43 ALDEHYDE)

[0094] METHYL EPI JASMONATE)

[0095] (4-isopropylphenyl)methanol (e.g. 8-methyl-l-oxaspiro[4.5]decan-2- 2.53 1.71 CUMIN YL ALCOHOL) one (e.g. METHYL LAITONE) 2,4-dimethylcy clohex-3 -ene- 1 - 2.36 methyl 2-methylbutanoate 1.55 carbaldehyde (e.g. CYCLAL C)

[0096] 4-(4-hydroxy-4-methylpentyl)cyclohex-3- methyl 2-phenylacetate (e.g.

[0097] 2.15 1.82

[0098]

[0099] enecarbaldehyde (e.g. CYCLOHEXAL) METHYL PHENYL ACETATE)6-pentyltetrahydro-2H-pyran-2-one (e.g. methyl 2-hydroxybenzoate (e.g.

[0100] 2.39 2.33 DECALACTONE DELTA) METHYL SALICYLATE)

[0101] 4-methyl-5-pentyldihydrofuran- 5-hexyloxolan-2-one (e.g.

[0102] 2.36 2(3H)-one (e g. METHYL 2.35 DECALACTONE GAMMA)

[0103] TUBERATE)

[0104] 2-methoxy-4-propylphenol (e.g. 3,7-dimethyl-2,6-octadien-l-ol 2.88 2.97 DIHYDRO EUGENOL) (e.g. NEROL)

[0105] methyl 2-(methylamino)benzoate (e.g. (2Z)-3,7-dimethylocta-2,6-dien-l- 2.66 2.97 DIMETHYL ANTHRANILATE) ol (e.g. NEROLEX)

[0106] 2-m ethyl- 1 -phenylpropan-2-ol (e.g. 1 -(3 -methylbenzofuran -2- 2.04 2.64 DIMETHYL BENZYL CARBINOL) yl)ethanone (e.g. NEROLIONE) 2-methyl-4-phenylbutan-2-ol (e.g.

[0107] (2E,6Z)-nona-2,6-dienal (e.g.

[0108] DIMETHYL PHENYL ETHYL 2.42 2.68

[0109] NONADIENAL)

[0110] CARBINOL)

[0111] (2Z,6E)-2,6-nonadien-l-ol (e.g.

[0112] 2,6-dimethylheptan-2-ol (e.g. DIMETOL) 2.99 2.70

[0113] NONADIENOL-2,6)

[0114] ethyl benzoate (e.g. ETHYL 5-pentyloxolan-2-one (e.g.

[0115] 2.64 1.83 BENZOATE) NONALACTONE GAMMA)

[0116] (Z)-non-6-en-l-ol (e.g.

[0117] ethyl butanoate 1.77 2.98

[0118] NONENOL-6-CIS)

[0119] ethyl 2-methylpropanoate (e.g. ETHYL 7-methoxy-3,7-dimethyloctan-2-ol 1.55 2.03 ISOBUTYRATE) (e.g. OSYROL)

[0120] 8-ethyl-l-oxaspiro[4.5]decan-2-one (e.g. 5-heptyldihydrofuran-2(3H)-one 2.24 2.89 ETHYL LAITONE) (e.g. PEACH PURE)

[0121] ethyl 3-phenyloxirane-2-carboxylate (e.g. 2-(o-tolyl)ethanol (e.g.

[0122] 2.43 1.78 ETHYL PHENYL GLYCID ATE) PEOMOSA)

[0123] 2-(phenoxy)ethyl 2- ethyl 2-hydroxybenzoate (e.g. ETHYL

[0124] 2.86 methylpropanoate (e.g. 2.92 SALICYLATE)

[0125] PHENIRAT)

[0126] 2-ethyl-3 -methylpyrazine (e.g. ETHYL 2-phenyl-ethanal (e.g. PHENYL 1.65 1.74 METHYL PYRAZ) ACETALDEHYDE)

[0127] 4-allyl-2-methoxyphenol (e.g.

[0128] 2.40 2-phenylethyl acetate 2.28 EUGENOL)

[0129] 4-allyl-2-methoxyphenyl acetate (e.g.

[0130] 2.30 2-phenylethyl formate 1.83 EUGENYL ACETATE)

[0131] 3-(4-methoxyphenyl)-2-methylpropanal 3-phenylpropanal (e.g. PHENYL 2.32 1.87 (e.g. CANTHOXAL) PROPIONIC ALDEHYDE)

[0132] 3-phenylpropan-l-ol (e.g.

[0133] methyl oct-2-ynoate (e.g. FOLIONE) 2.72 1.71

[0134] PHENYL PROPYL ALCOHOL) 4-isopropylcyclohexanol (e.g. 3-methylbut-2-en-l-yl acetate

[0135] 2.71 1.88 FOLROSIA) (e.g. PRENYL ACETATE)

[0136] 2-ethoxy-4- ethyl 2-(2,4-dimethyl- 1 ,3 -dioxolan-2- 1.68 (isopropoxymethyl)phenol (e.g. 2.35 yl)acetate (e g. FRAGOLAN)

[0137] PROPYL DIANTILIS)

[0138] diethyl cyclohexane-l,4-dicarboxylate (E)-5-methylheptan-3-one oxime 2.13 2.64 (e.g. FRUCTALATE) (e.g. STEMONE)

[0139] N,2-dimethyl-N-phenylbutanamide (e.g. ethyl methyl phenyl glycidate (e.g.

[0140] 2.47 2.95 CISTULATE) STRAWBERRY PURE)

[0141] (E)-3,7-dimethylocta-2,6-dien-l-ol (e.g. 2-(p-tolyl)acetaldehyde (e.g.

[0142] 2.97 2.28

[0143]

[0144] GERANIOL) S YRINGA ALDEHYDE)2-(2-hydroxypropan-2-yl)-5- 4-methyl-l-propan-2-ylcyclohex- methylcyclohexanol (e.g. 1.68 2.74

[0145] 3-en-l-ol (e g. TERPINEN-4-OL) GERANODYLE)

[0146] 2-(4-m ethyl- 1 -cyclohex-3 - methyl-3 -oxo-2 -pentylcyclopentane

[0147] 2.91 enyl)propan-2-ol (e.g. 2.63 acetate (e g. HEDIONE)

[0148] TERPINEOL ALPHA)

[0149] 2-(4-m ethylcyclohex-3 -en- 1 - heptanone-2 1.91 2.63 yl)propan-2-ol (e.g. LINDENOL)

[0150] 4-methylbenzaldehyde (e.g.

[0151] nonanal (e g. ALDEHYDE C 9) 1.90 1.99 TOLYL ALDEHYDE PARA)

[0152] 2,4-dimethylcyclohex-3- (E)-hex-2-enal (e.g. HEXENAL-2

[0153] 1.58 enecarbaldehyde (e.g. 2.36 TRANS)

[0154] LIGUSTRAL)

[0155] (E)-hex-2-en-l-ol (e.g. HEXENOL 3 -phenylbutanal (e.g.

[0156] 1.60 2.27 TRANS-2) TRIFERN AL)

[0157] 3-(benzo[d][l,3]dioxol-5-yl)-2- (Z)-hex-3-en-l-yl acetate (e.g.

[0158] 2.34 methylpropanal (e.g. 2.37 HEXENYL-3-CIS ACETATE)

[0159] TROPIONAL)

[0160] 6-hexyltetrahydro-2H-pyran-2-one undec- 10-enenitrile (e.g. VIOLIFF) 2.77 (e g. UNDECALACTONE 2.92

[0161]

[0162] DELTA)

[0163] Group B perfume ingredients include a broad selection of odoriferous substances that are well known to the person skilled in the art. Non-limiting examples include (l-methyl-2-(((lR,3R)-2,2,3-trimethylcyclopentyl)methyl)cyclopropyl)methanol (e.g. PASHMINOL); (l-methyl-2-((l,2,2-trimethylbicyclo[3.1.0]hexan-3-yl)methyl)cyclopropyl)methanol (e.g. JAVANOL); (lR,2S,4R)-2'-isopropyl-l,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,4'-[l,3]dioxane] (e.g. BELAMBRE); (lR,6S,8aS)-6-methoxy-l,4,4,6-tetramethyloctahydro-lH-5,8a-methanoazulene (e.g. CEDRYL METHYL ETHER); (lS,2R,4R)-l,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (e.g. FENCHYL ALCOHOL); (lS,2R,5R)-2-ethoxy-2,6,6-trimethyl-9-methylenebicyclo[3.3.1]nonane (e.g. BOISIRIS); (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (e.g. BORNEOL); (lS,8aR)-l,4,4,6-tetramethyl-2,3,3a,4,5,8-hexahydro-lH-5,8a-methanoazulene (e.g. CEDRENE); (2E,5E)-5,6,7-trimethylocta-2,5-dien-4-one (e.g. POMAROSE); (2E,6Z)-3,7-dimethylnona-2,6-dienenitrile (e.g. LEMONILE); (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-lH-benzo[e][l]benzofuran (e.g. AMBROFIX); (3-pentyloxan-4-yl) acetate (e.g. AKIGALAWOOD); (4aR,5R,7aS,9R)-Octahydro-2,2,5,8,8,9a-hexamethyl-4H-4a,9-methano-azuleno[5,6-d]-l,3-di oxole (e.g. AMBROCENIDE); (4-isopropylcy cl ohexyl)m ethanol (e.g. MAYOL); (4Z)-hept-4-en-2-yl 2-hydroxybenzoate (e.g. KARMAFLOR); (5R,10R)-6,10-dimethyl-2-(propan-2-ylidene)-spiro[4.5]dec-6-en-8-ol (e.g. VETIVENOL); (E)-l-(2,6,6-trimethyl-l-cyclohexenyl)but-2-en-l-one (e.g. DAMASCONE BETA); (E)-l-(2,6,6-trimethylcyclohex-2-en-l-yl)but-2-en-l-one (e.g.DAMASCONE ALPHA); (E)-l-(2,6,6-trimethylcyclohexa-l,3-dien-l-yl)but-2-en-l-one (e.g. DAMASCENONE); (E)-l,2-dimethoxy-4-(prop-l-en-l-yl)benzene (e.g. METHYL ISOEUGENOL); (E)-l -methoxy -4-(prop-l-en-l-yl)benzene (e.g. ANETHOLE); (E)-2-((3,5-dimethylhex-3-en-2-yl)oxy)-2-methylpropyl cyclopropanecarboxylate (e.g. SYLKOLIDE); (E)-2 -benzylideneoctanal (e.g. HEXYL CINNAMIC ALDEHYDE); (E)-2-ethoxy-5-(prop-l-en-l-yl)phenol (e.g. VANITROPE); (E)-2-ethyl-4-(2,2,3-trimethylcyclopent-3-en-l-yl)but-2-en-l-ol (e.g. RADJANOL); (E)-2-methyl-4-(2,2,3-trimethyl-l-cyclopent-3-enyl)but-2-en-l-ol (e.g. S ANTACORE); (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol (e.g. POLYSANTOL); (E)-3,7-dimethylnona-l,6-dien-3-ol (e.g. ETHYL LINALOOL); (E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-l-yl)but-3-en-2-one (e.g. IRISANTHEME); (E)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-l-yl)pent-4-en-2-ol (e.g. EBANOL); (E)-4-(2,5,6,6-tetramethylcyclohex-2-en-l-yl)but-3-en-2-one (e.g. IRONE ALPHA); (E)-4-(2,6,6-trimethyl-l-cyclohex-2-enyl)but-3-en-2-one (e.g. IRISONE ALPHA); (E)-4-(2,6,6-trimethylcyclohex-l-en-l-yl)but-3-en-2-one (e.g. IONONE BETA); (E)-4-methyldec-3-en-5-ol (e.g. UNDECAVERTOL)(E)-4-methyldec-3-en-5-ol (e g. UNDECAVERTOL); (E)-6-ethyl-3-methyloct-6-en-l-ol (e.g. SUPER MUGUET); (E)-dec-2-enal (e.g. DECENAL-2 TRANS); (E)-dec-4-enal (e.g. DECENAL-4-TRANS); (E)-methyl 2-((7-hydroxy-3,7-dimethyloctylidene)-amino)benzoate (e.g. AURANTIOL); (E)-methyl non-2-enoate (e.g. NEOFOLIONE); (E)-non-2-enal (e.g. ALDEHYDE C 90 NONENYLIC); (E)-oxacyclohexadec-12-en-2-one (e.g. HABANOLIDE); (E)-undec-9-enenitrile (e.g. FLORIDILE); (ethoxymethoxy)cyclododecane (e g. BOISAMBRENE FORTE); (Z)-l-(cyclooct-3-en-l-yl)propan-l-ol (e.g. FLORYMOSS); (Z)-l,l-diethoxy-3,7-dimethylocta-2,6-diene (e.g. CITRATHAL R); (Z)-3,7,ll-trimethyldodeca-6,10-dienal (e.g. DIHYDRO FARNESAL); (Z)-3-methylcyclopentadec-5-enone (e.g. MUSCENONE); (Z)-cyclohexadec-5-enone (e.g. VELVIONE); (Z)-dec-4-enal (e.g. DECEN-1-AL, CIS-4-); (Z)-hex-3-en-l-yl 2-hydroxybenzoate (e.g. HEXENYL-3-CIS SALICYLATE); (Z)-oxacycloheptadec-10-en-2-one (e.g. AMBRETTOLIDE); [2-[l-(3,3-dimethylcyclohexyl)-ethoxy]-2-methylpropyl]propanoate (e.g. HELVETOLIDE); l-((lS,8aS)-l,4,4,6-tetramethyl-2,3,3a,4,5,8-hexahydro-lH-5,8a-methanoazulen-7-yl)ethanone (e.g. VERTOFIX COEUR); l-((2-(tert-butyl)cyclohexyl)oxy)butan-2-ol (e.g. AMBER CORE); l-(l,2,8,8-tetramethyl-l,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanone (e.g. GEORGYWOOD); l-(2,2,6-trimethylcyclohexyl)hexan-3-ol (e.g. NIMBEROL); l-(2,3,8,8-tetramethyl-l,2,3,4,5,6,7,8-octahydronaphthalen-2-yl)ethanone (e.g. ISO E SUPERS, ISO GAMMA SUPER); 1 -(2,6,6-trimethyl-1 -cyclohex-3 -enyl)but-2-en-l -one (e.g. DAMASCONE DELTA); l-(5,5-dimethylcyclohex-l-en-l-yl)pent-4-en-l-one (e.g. GALBANONE); 1, 1,2,3, 3-pentamethyl-2,3,6,7-tetrahydro-lH-inden-4(5H)-one (e.g. CASHMERAN); l,2,4-trimethoxy-5-propylbenzene(e.g. CALMODE); l,4-dioxacycloheptadecane-5, 17-dione (e.g. ETHYLENE BRAS SYL ATE); 1-butoxy-l-oxopropan-2-yl butanoate (e.g. BUTYL BUTYRO LACTATE); l-methyl-2-(5-methylhex-4-en-2-yl)cyclopropylmethanol (e.g. ROSYFOLIA); 2-(l-(3,3-dimethylcyclohexyl)ethoxy)-2-methylpropyl cyclopropanecarboxylate (e.g. SERENOLIDE); 2-(4-methylcyclohexyl)propan-2-ol (e.g. DIHYDRO TERPINEOL)2-(tert-butyl)cyclohexyl acetate (e.g. AGRUMEX); 2,2,6-trimethylcyclohexyl-3-hexanol (e.g. TIMBEROL); 2,2-dimethyl-3-(m-tolyl)propan-l-ol (e.g. MAJANTOL); 2,3,3-trimethyl-l-indanone (e.g. SAFRALEINE); 2,4-dimethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-l,3-dioxolane (e.g. OKOUMAL); 2,5,5-trimethyl-l,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol (mixture of isomers) (e.g. AMBRINOL); 2,5,5-trimethyl-l,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol (mixture of isomers) (e g. AMBRINOL); 2,6-dimethyloct-7-en-2-ol (e.g. DIHYDRO MYRCENOL); 2,6-dimethyloct-7-en-2-ol (e.g. FLORALYM); 2-cyclohexylidene-2-(o-tolyl)acetonitrile (e.g. PETALIA); 2-cyclohexylidene-2-phenyl-acetonitrile (e.g. PEONILE); 2-ethoxynaphthalene (e.g. NEROLIN); 2-ethyl-N-methyl-N-(m-tolyl)butanamide (e.g. PARADISAMIDE); 2-isopropyl-5-methylcyclohexanol (e.g. MENTHOL); 2-isopropyl-5-methylphenol (e.g. THYMOL CRYSTALS); 2-methoxynaphthalene (e.g. YARA YARA); 2-methylpropyl 2-hydroxybenzoate (e g. ISOBUTYL SALICYLATE); 2-methylundecanal (e g. ALDEHYDE C 12 MNA); 3-(2-m ethylpropyl)- 1 -methylcyclohexanol (e.g. ROSSITOL); 3-(4-(2-methylpropyl)-2-methylphenyl)propanal (e.g. NYMPHEAL); 3-(4-ethylphenyl)-2,2-dimethylpropanal (e.g. FLORALOZONE); 3-(4-methylcyclohex-3-en-l-yl)butan-l-ol (e.g. CYCLOMETHYLENE CITRONELLOL); 3-(benzo[d][l,3]dioxol-5-yl)-2-methylpropanal (e.g. TROPIONAL); 3,5,5-trimethylhexan-l-ol (e.g. ISONONANOL); 3,7-dimethyloct-6-en-3-ol (e.g. DIHYDRO LINALOOL); 3,7-dimethyloct-6-enenitrile (e.g. CITRONELLYL NITRILE); 3,7-dimethylocta-l,6-dien-3-yl acetate (e.g. LINALYL ACETATE); 3,7-dimethylocta-l,6-dien-3-yl dimethylcarbamate (e.g. PEPPERWOOD); 3,7-dimethyloctan-l-ol (e.g. PELARGOL); 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-l-yl)pentan-2-ol (e.g. SANDALORE); 3-methyl-5-phenylpent-2-enenitrile (e.g. CITRONITRILE); 3-methyl-5-phenylpentan-l-ol (e.g. MEFROSOL); 4-(l-ethoxyethenyl)-3,3,5,5-tetramethylcyclohexan-l-one (e.g. KEPHALIS); 4-(2,6,6-trimethylcyclohex-l-en-l-yl)butan-2-one (e.g. DIHYDRO IONONE BETA); 4, 6, 6, 7, 8, 8-hexamethyl-l,3,4,6,7,8-hexahydrocyclopenta[g]isochromene (e.g. GALAXOLIDE); 4-isopropylbenzonitrile (e.g. CUMIN NITRILE); 4-methyl-2-(2-methylprop-l-en-l-yl)tetrahydro-2H-pyran (e.g. ROSE OXIDE CO); 4-methyl-2-phenyl-3,6-dihydro-2H-pyran (e.g. ROSYRANE); 5-isopropyl-2-methylphenol (e.g. CARVACROL); 5-octyloxolan-2-one (e.g. DODECALACTONE GAMMA); 5-pentyldihydrofuran-2(3H)-one (eg. PRUNOLIDE); 6,6-dimethoxy-2,5,5-trimethylhex-2-ene (e.g. METHYL PAMPLEMOUSSE); 6,8-dimethylnonan-2-ol (e.g. NONADYLE); 6-heptyltetrahydro-2H-pyran-2-one (e g. DODECALACTONE DELTA); 7-isopentyl-2H-benzo[b][l,4]dioxepin-3(4H)-one (e.g. AZURONE)7-isopentyl-2H-benzo[b][l,4]dioxepin-3(4H)-one (e.g. AZURONE)benzyl 2-hydroxybenzoate (e.g. BENZYL SALICYLATE); cyclohexyl 2-hydroxybenzoate (e.g. CYCLOHEXYL SALICYLATE); dec-9-en-l-ol (e.g. ROSALVA); decahydro-2,2,6,6,7,8,8-heptamethyl indenofuran (e.g. AMBER XTREM); dodecan-l-ol (e.g. ALCOHOL C 12 LAURIC); hexyl 2-hydroxybenzoate (e.g. HEXYL SALICYLATE); methyl non-2-ynoate (e.g. METHYL OCTYNE CARBONATE); Mixture of isomers (E)- and (Z)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-l-yl)-3-buten-2-one, and (E)-l-(2,6,6-trimethylcyclohex-2-en-l-yl)pent-l-en-3-one (e.g. ISORALDEINE); nonan-l-ol (e.g. ALCOHOL C 9 NONYLIC); oxacyclohexadecan-2-one (e g. THIBETOLIDE); pentyl 2-hydroxybenzoate (e.g. AMYL SALICYLATE); pentyl 2-hydroxybenzoate (e.g. AMYL SALICYLATE); prop-2-enyl 3 -cycloh exylpropanoate (e.g. ALLYL CYCLOHEXYL PROPIONATE); prop-2-enyl heptanoate (e.g. ALLYL OENANTHATE); and mixtures thereof. Group B perfume ingredients include natural, essentially apolar essential oils and extracts. Such apolar oils may be selected from Lemon oils, Lime oils, Mandarin oils, Orange oils, Tangerine oils, Grapefruit oils, Bergamot oils, Bigarade oil, Petit grain oils, Rose oils, Ylang ylang oils, Jasmin absolutes, Jacinth extracts, Magnolia oils, Angelica seed oils, Tuberose absolutes, Cypress oils, Davana oils, Elemi oils, Violet leaf oils, Buchu leaf oils, Galbanum oils, Juniper oils, Geranium oils, Clary sage oils, Costus oil, Eucalytptus oils, Lavandin oils, Lavender oils, Myrrh oils, Neroli oils, Opoponax oils, Mint oils, Peppermint oils, Spearmint oils, Fennel oils, Ginger oils, Nutmeg oils, Clove oils, Pepper oils, Rosemary oils, Thyme oils, Cardamom seed oils, Chamomile oils, Vetiver oils, Broom absolutes, Birch leaf oils, Cedar wood oils, Sandal wood oils, Oakmoss oils, Pine oils, Tea tree oils, Tamarin oils, Patchouli oils, and mixtures thereof.

[0164] In addition to those perfume ingredients and solvents referred to hereinabove additional perfume ingredients may be employed in perfume oils according to the invention depending upon the particular hedonic or functional effect that a perfumer is trying to achieve. A comprehensive list of perfume ingredients that may be used in the preparation of a perfume oil in accordance with the present invention may be found in the perfumery literature, for example “Perfume & Flavor Chemicals”, S. Arctander S. Arctander Perfume and Flavor Chemicals (Aroma Chemicals) Vol 1, lulu.com, 2017; Vol 2, lulu.com 2019 and Vol 3, lulu.com 2019, or on the Internet, for example http: / / www.thegoodscentscompany.com / (consulted on October 30, 2024).

[0165] In addition to these perfume ingredients, perfume oils according to the present invention may contain other functional ingredients commonly used in perfumery. Such ingredients may include,but are not limited to additives, such as, one or more solvents having a ClogP higher than 1.5, one or more antioxidants, one or more buffers, one or more dyes, as well as mixtures thereof.

[0166] As stated herein above, the second aspect of the invention is concerned with the perfume oil that is presented in the form in which the perfume oil is separated into functionally interacting first and second parts.

[0167] The ingredients contained in first and second parts are not merely randomly selected combinations of perfume ingredients that when aggregated form the perfume oil. The separate parts are cooperative along both hedonic and functional axes, in the sense that neither part alone would be considered to be a finished perfume oil having a coherent odour by a skilled perfumer. Further, if all of the ingredients contained in the aggregate of the separate parts were mixed together in random order without any regard for the mixing instructions according to the invention, the aggregate mixture would not function as an acceptable finished perfume oil, not least because it would contain a precipitate or undissolved material. This would at the very least be unsightly and undesirable for that reason, and may even interfere with the efficient incorporation of the perfume oil into a consumer product base, for example, by fouling mixing lines during a manufacturing operation. Only by separating the ingredients into the aforementioned functionally interacting and cooperating parts as described herein can the skilled person create a perfume oil with acceptable hedonics that functions correctly in its intended application.

[0168] Perfume oils presented in the form of functionally interacting first and second parts may comprise instructions for assembly of the cooperating parts in the manner described herein, which instructions may be related to any stage of the perfume oil’s lifecycle. For example, the first and second parts may be combined during an operation at the stage of formulation by a perfumer, during scale-up and manufacturing, during distribution or even by a consumer before use.

[0169] In particular embodiments, the weight ratio of first part to second part in the perfume oil is from 0.25 to 10, more particularly from 0.4 to 6, still more particularly from 0.5 to 4.

[0170] In accordance with the invention, the absolutes and optionally Group Al ingredients contained in the first part are dissolved in the first part by means of the polar solvent and any cooperating Group A2 ingredients before being combined with the second part containing Group B ingredients. Accordingly, in particular embodiments of the second aspect of the invention the perfume oil is provided in the form that comprises separate parts, wherein the first part comprises the difficult to solubilize perfume ingredients, one or more polar solvent, optionally one or more Group A2 ingredients, and is absent of any Group B ingredients.In more particular embodiments, in the first part the sum of the concentration of the at least one absolute, the Group Al perfume ingredients and the Group A2 perfume ingredients is from 25 to 95 wt.%, based on the total weight of the first part, and wherein the ratio of the sum of the concentration of at least one absolute and Group Al perfume ingredients to the at least one polar solvent is from 0.2 to 5, more particularly from 0.5 to 2.5.

[0171] In still more particular embodiments, in the first part comprises (by weight of the first part): - 0.5 to 25 wt.% of at least one absolute;

[0172] - 0 to 50 wt.% of a Group Al perfume ingredient;

[0173] - 0 to 50 wt % of a Group A2 perfume ingredient;

[0174] - 5 to 75 wt % of at least one polar solvent having a ClogP of 1.5 or less;

[0175] wherein the sum of the concentrations of the at least one absolute, Group Al perfume ingredients and Group A2 perfume ingredients is from 25 to 95 wt.%; and wherein the ratio of the sum of the concentration of the at least one absolute and the Group Al perfume ingredient to the at least one polar solvent is from 0.2 to 5.

[0176] In a particular embodiment, the first part comprises 0.1 to 25 wt.%, more particularly 0.5 to 10 wt.% of Tonka bean resinoid based on the weight of the first part.

[0177] In a particular embodiment, the first part comprises 0.1 to 25 wt.%, more particularly 0.5 to 10 wt.% of Myrrh resinoid based on the weight of the first part.

[0178] In a particular embodiment, the first part comprises 0.1 to 25 wt.%, more particularly from 0.5 to 10 wt.% of benzoin resinoid based on the weight of the first part.

[0179] In a particular embodiment, the first part comprises 0.1 to 25 wt.%, more particularly from 0.5 to 10 wt.% of cistus absolute based on the weight of the first part.

[0180] In a particular embodiment, the first part comprises 0.1 to 25 wt.%, more particularly from 0.5 to 10 wt.% of solid cocoa extracts based on the weight of the first part.

[0181] In particular embodiments, the first part comprises from 1 to 50 wt.%, more particularly from 5 to 50 wt.% of Group A2 ingredients, based on the weight of the first part.

[0182] In particular embodiments, the second part comprises (by weight of the second part) at least 80 wt.% of Group B perfume ingredients.

[0183] By providing the perfume oils in the form of separate but functionally cooperating parts described above one can produce perfume oils that contain very high levels of absolutes or other difficult tosolubilise solid ingredients that can deliver both interesting and impactful hedonics as well as delivering on sustainability objectives, whilst being economical with the levels of solvent.

[0184] In particular embodiments, the polar solvent may be employed in the first part in an amount ranging from 5 to 40 wt.%, still more preferably from 5 to 30 wt.% based on the total weight of the first part. Minimizing the amount of polar solvent in the first part has the advantage of reducing cost and, in case the polar solvent is of petrochemical origin, to enhance the naturality and sustainability of the perfume oil. Additionally, it may be advantageous, from a perfume performance standpoint, that a minimal amount of solvent is present in the perfume oil.

[0185] In particular embodiments of the invention, the first part may contain additional perfume ingredients, which ingredients may be used by the skilled perfumer to balance the hedonic of the perfume oil, and also contribute to its stability, in the sense of promoting the dissolution of the of difficult to solubilize ingredients.

[0186] Such perfume ingredients include but are not limited to dodecan-l-ol (e.g. ALCOHOL C 12 LAURIC); pentyl 2-hydroxybenzoate (e g. AMYL SALICYLATE); nonan-l-ol (e g. ALCOHOL C 9 NONYLIC); methyl non-2-ynoate (e g. METHYL OCTYNE CARBONATE); hexyl 2-hydroxybenzoate (e.g. HEXYL SALICYLATE); dec-9-en-l-ol (e.g. ROSALVA); cyclohexyl 2-hydroxybenzoate (e.g. CYCLOHEXYL SALICYLATE); benzyl 2-hydroxybenzoate (e.g. BENZYL SALICYLATE); 7-isopentyl-2H-benzo[b][l,4]dioxepin-3(4H)-one (e.g. AZURONE); 6-heptyltetrahydro-2H-pyran-2-one (e.g. DODECALACTONE DELTA); 6,8-dimethylnonan-2-ol (e g. NONADYLE); 5-octyloxolan-2-one (e g. DODECALACTONE GAMMA); 5-isopropyl-2-methylphenol (e.g. CARVACROL); 4-isopropylbenzonitrile (e.g. CUMIN NITRILE); 3-methyl-5-phenylpentan-l-ol (e.g. MEFROSOL); 3-methyl-5-phenylpent-2-enenitrile (e.g. CITRONITRILE); 3,7-dimethyloctan-l-ol (e.g. PELARGOL); 3,7-dimethylocta-l,6-dien-3-yl dimethylcarbamate (e.g. PEPPERWOOD); 3,7-dimethyloct-6-enenitrile (e.g. CITRONELLYL NITRILE); 3,7-dimethyloct-6-en-3-ol (e.g. DIHYDRO LINALOOL); 3,5,5-trimethylhexan-l-ol (e.g. ISONONANOL); 3-(4-methylcyclohex-3-en-l-yl)butan-l-ol (e.g. CYCLOMETHYLENE CITRONELLOL); 3 -(2-methylpropyl)-l -methylcyclohexanol (e.g. ROSSITOL); 2-phenylethyl 2-hydroxybenzoate (e.g. ); 2-methylpropyl 2-hydroxybenzoate (e.g. ISOBUTYL SALICYLATE); 2-methoxynaphthalene (e.g. YARA YARA); 2-isopropyl-5-methylphenol (e.g. THYMOL CRYSTALS); 2-isopropyl-5-methylcyclohexanol (e.g. MENTHOL); 2-ethyl-N-methyl-N-(m-tolyl)butanamide (e.g. PARADISAMIDE); 2-ethoxynaphthalene (e.g. NEROLIN CRYSTALS); 2-cyclohexylidene-2-phenylacetonitrile (e.g. PEONILE); 2,6-dimethyloct-7-en-2-ol (e.g. FLORALYM); 2,6-dimethyloct-7-en-2-ol (e g. DIHYDRO MYRCENOL); 2,5,5-trimethyl-l,2,3,4,4a,5,6,7-octahydronaphthalen-2-ol (mixture of isomers) (e.g. AMBRINOL); 2,2-dimethyl-3-(m-tolyl)propan-l-ol (e.g. MAJANTOL); 2-(4-methylcyclohexyl)propan-2-ol (e.g. DIHYDRO TERPINEOL); l-methyl-2-(5-methylhex-4-en-2-yl)cyclopropylmethanol (e.g. ROSYFOLIA); 1-butoxy-l-oxopropan-2-yl butanoate (e.g. BUTYL BUTYRO LACTATE); l,2,4-trimethoxy-5-propylbenzene (e.g. CALMODE); (Z)-hex-3-en-l-yl 2-hydroxybenzoate (e.g. HEXENYL-3-CIS SALICYLATE); (Z)-dec-4-enal (e.g. DECEN-l-AL, CIS-4-); (Z)-l,l-diethoxy-3,7-dimethylocta-2,6-diene (e.g. CITRATHALR); (Z)-l-(cyclooct-3-en-l-yl)propan-l-ol (e.g. FLORYMOSS); (E)-undec-9-enenitrile (e g. FLORIDILE); (E)-non-2-enal (e.g. ALDEHYDE C 90 NONENYLIC); (E)-methyl 2-((7-hydroxy-3,7-dimethyloctylidene)amino)benzoate (e.g. AURANTIOL); (E)-dec- 4-enal (e.g. DEGEN AL-4-TRANS); (E)-dec-2-enal (e.g. DECENAL-2 TRANS); (E)-6-ethyl-3-methyloct-6-en-l-ol (e.g. SUPER MUGUET); (E)-4-methyldec-3-en-5-ol (e.g. UNDEC AVERTOL); (E)-2-methyl-4-(2, 2, 3-trimethyl- 1-cy cl opent-3 -enyl)but-2-en-l-ol (e.g. S ANTACORE); (E)-2-ethoxy-5-(prop-l-en-l-yl)phenol (e.g. PROPENYL GUAETHOL (VANITROPE)); (E)-l-methoxy-4-(prop-l-en-l-yl)benzene (e g. ANETHOLE SYNTHETIC); (E)-l,2-dimethoxy-4-(prop-l-en-l-yl)benzene (e.g. METHYL ISOEUGENOL); (5R,10R)-6,10-dimethyl-2-(propan-2-ylidene)spiro[4.5]dec-6-en-8-ol (e.g. VETIVENOL); (4Z)-hept-4-en-2-yl 2-hydroxybenzoate (e.g. KARMAFLOR); (4-isopropylcyclohexyl)methanol (e.g. MAYOL); (2E,6Z)-3,7-dimethylnona-2,6-dienenitrile (e.g. LEMONILE); (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (e.g. BORNEOL CRYSTALS); (1S,2R,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol (e.g. FENCHYL ALCOHOL); and mixtures thereof.

[0187] The third aspect of the invention is related to a method of manufacturing a perfume oil defined in the first and second aspects of the invention.

[0188] As stated above, the method comprises the step of providing first and second functionally cooperating parts, and blending them together to provide a finished perfume oil. The first part comprises the absolute, optionally Group Al perfume ingredients, the polar solvent and optionally Group A2 perfume ingredients and the weight ratio of the sum of the absolute and Al perfume ingredients to the polar solvent is from 0.2 to 5. The second part comprises the Group B ingredients.

[0189] Once the absolute and any Group Al ingredients in the first oil part are dissolved, the first and second parts can be blended together to form the perfume oil.

[0190] In particular embodiments, the method according to the invention comprises the steps of:

[0191] 1) Providing a first part comprising, based on the total weight of the first part:

[0192] 0.5 to 25 wt.% of at least one absolute;

[0193] 0 to 50 wt.% of a Group Al perfume ingredient;0 to 50 wt % of a Group A2 perfume ingredient;

[0194] 5 to 75 wt % of at least one polar solvent having a ClogP of 1.5 or less;

[0195] wherein the sum of the concentrations of the at least one absolute, any perfume ingredients drawn from Group Al and any ingredients drawn from group A2 is from 25 to 95 wt.%, based on the total weight of the first part; and wherein the ratio of the sum of the concentration of the at least one absolute and any perfume ingredients drawn from Group Al to the at least one polar solvent is from 0.2 to 5;

[0196] 2) Providing a second part comprising, by weight of the second part, at least 80 wt.% of Group B perfume ingredients;

[0197] 3) Dissolving the absolute and any Group Al ingredients in the polar solvent and / or the polar solvent mixed with any Group A2 ingredients; and

[0198] 4) Blending the first part containing the dissolved absolutes and any Group Al ingredients in the second part comprising at least one Group B perfume ingredient to form the perfume oil. The first part may be formed by adding its constituent into a mixing vessel and mixing them until a clear and homogeneous mixture is obtained. The manner and order in which the ingredients are added to a vessel and mixed may vary depending upon the physical form of the ingredients. For example, dissolution of solid ingredients can be facilitated by kneading and stirring. For those ingredients that are solid, and in particular those that are crystalline, they can be melted by the application of heat before mixing with other perfume ingredients and polar solvents. In more particular embodiments, the absolutes can be added to the vessel in the form of a stock solution, as described herein.

[0199] The second part may be prepared in a similar manner before combining with the first part so formed.

[0200] The first and second oil parts, as stated herein above, would not be recognised by a skilled perfumer as finished perfume oils. Rather, they represent component parts of a perfume oil which is constituted when the component parts are combined in the manner described herein. The first and second parts may be stored separately before combination for a period of hours, days or months, or they may be prepared and combined contemporaneously.

[0201] The first and second parts may be combined during any operation. For example, the combination may occur during the formulation of the perfume oil by a perfumer, or it may be carried out during the manufacture of the perfume oil, during its distribution, or it can even be carried out by a consumer before use. Still further, the first and second parts may be combined with a consumerproduct base, such as an aqueous base comprising surfactants or a hydro-alcoholic solvent, in order to form a perfumed consumer product.

[0202] Perfume oil according to the invention are storage stable at a temperature in the range of 10°C to 25 °C, more particularly from 10°C to 15°C, more particularly from 11°C to 13°C. Furthermore, in stress tests the first and second parts of the perfume oil remain homogeneous and transparent when submitted to a temperature of -11°C for 48 hours, 5°C for 2 weeks and 50 °C for 2 weeks. The use of a mixture of at least one polar solvent having a ClogP lower than 1.5 and optionally a Group A2 perfume ingredient as a solubilizing aid for absolutes and Group Al ingredients, wherein the ratio of the sum of the concentration of absolutes and Group Al ingredients to the polar solvent is from 0.2 to 5, represents a fourth aspect of the invention.

[0203] Another related aspect of the invention is concerned with stock solutions of any of the absolutes, Group Al ingredients referred to herein above, or mixtures thereof, in which the ratio of the sum of the concentration of absolutes and Group Al ingredients to the polar solvent referred to above is from 0.2 to 5.

[0204] The perfume oils defined herein above can be incorporated into consumer product bases to provide perfumed consumer products, which consumer products represent the fifth aspect of the invention. The perfumed consumer products include but are not limited to fine fragrance, eau de parfum, cologne, after shave, shave cream, shave gel, deodorant and antiperspirant in the form of spray, stick, roll-on, soap or powder, oral care product, toothpaste flavor, breath freshener, oral rinse, tooth whitener, denture adhesive, disinfectant, personal care, product, cleanser, soap, bar or liquid soap, body wash, body milk, body cream, hand sanitizer, hand wash, sunscreen product, lotion, shower gel, bath salt, liquid shampoo, solid shampoo, liquid hair care conditioner, solid hair care conditioner, hair rinse, hair refresher, hair fixative, hair styling or styling aid, hair dying product, and feminine hygiene product.

[0205] In particular embodiments of the invention there is provided a cosmetic product, such as skin care cream, lotion and serum, foundation, lipstick, mask, anti-ageing product, exfoliating scrub, foot cream, facial tissue, cleansing wipe, and talc, comprising a perfume composition as defined herein. In particular embodiments of the invention there is provided a household care product, such as hard surface cleaner, all-purpose cleaner, dish wash liquid, automatic dish wash detergent and single dose detergent, toilet cleaner, rim block, wipe, foam, liquid refresher, air refresher, room deodorizer, candle, air scenting device, plug-in, aerosol, non-aerosol dispenser, and weed comprising a perfume composition as defined herein.In particular embodiments of the invention there is provided a fabric care product, such as laundry detergent in powder, liquid, bar or single dose form, fabric softener in liquid or sheet, or powder form, drier sheet, fabric refresher, scent booster, ironing water comprising a perfume composition as defined herein.

[0206] In particular embodiments of the invention the perfumed product comprises a perfume composition as herein described, and a container and / or packaging and / or labelling, which container, packaging or labelling contains branded wording and / or logo that is associated with said perfume composition.

[0207] In particular embodiments of the invention, the perfume oil may be incorporated into a consumer product in an amount in the range of 0.01 to 50 wt.%, more particularly from 0.1 to 25 wt.%, still more particularly from 1 to 15 wt.%, based on the total weight of the consumer product.

[0208] The present invention is further illustrated by means of the following non-limiting examples. EXAMPLES

[0209] Example 1. Preparation of a perfume oil comprising 20,9 wt. % of absolutes and Group Al ingredients

[0210] In this example, a perfume oil composition 1 is prepared by mixing the perfume ingredients and solvents shown in Table 3. The percentages of the ingredients and solvents are also reported in Table 3. The fourth column shows the composition of the perfume oil composition showing solubility issues (comparative example), while the fifth and sixth columns show the perfume oil composition comprising first and second parts after splitting according to the present invention. The first part to second part weight ratio is 0.79.

[0211] Table 3. Solubility of perfume oil composition 1 and of its first part (44 wt.% of the perfume oil) of the complete perfume oil and second part (56 wt.% of the perfume oil).

[0212] Physical Complete First Second Perfumery Ingredient ClogP state at perfume Part Part

[0213] 25 °C [wt.%] [wt.%] [wt.%] HEDIONE 2.91 Liquid 9.4 21.4

[0214] VANILLIN 1.28 Solid 4 9.1

[0215] MAHONIAL 2.12 Liquid 1.6 3.6

[0216] ISOBUTAVAN 1.72 Liquid 0.4 0.9

[0217] Myrrh resinoid Solid 0.4 0.9

[0218] AUBEPINE PARA CRESOL 1.78 Liquid 0.6 1.4

[0219] Benzoin resinoid Solid 1 2.3

[0220] TRIETHYL CITRATE 1.17 Liquid 6.7 1.0

[0221] 1,3 -BUTANEDIOL Liquid 2 4.0

[0222]

[0223] COUMARIN PURE CRYSTALS 1.41 Solid 4 9.1ETHYL VANILLIN 1.81 Solid 2.8 6.4 HELIOTROPINE CRYSTALS 1.76 Solid 2 4.5

[0224] EVERNYL 2.73 Solid 3 6.8

[0225] ETHYL MALTOL 0.63 Solid 2.8 6.4

[0226] BICYCLO NONALACTONE 1.19 Liquid 2.4 5.5

[0227] Tonka Bean resinoid Solid 0.9 2.0

[0228] ISO GAMMA SUPER 4.85 Liquid 21.0 37.5 HELVETOLIDE 5.38 Liquid 12.3 22.0 AMBROFIX 5.47 Solid 4.4 7.9 CASHMERAN 4.00 Liquid 3.4 6.1 Mandarin oil Liquid 3.6 6.4 Patchouli oil Liquid 1.6 2.8 LINALYL ACETATE NAT 3.69 Liquid 1.6 2.8 AGRUMEX 4.06 Liquid 2.0 3.6 HEDIONE 2.91 Liquid 0.9 1.6 TROPIONAL 2.37 Liquid 0.6 1.1 Vetiver oil Liquid 0.8 1.4 IONONE BETA 3.77 Liquid 0.8 1.4 RADJANOL 4.63 Liquid 0.5 0.9 ANETHOLE NATURAL 3.31 Liquid 0.7 1.3 PEACH PURE 2.89 Liquid 1.3 2.3 Ci stus oil Liquid 0.4 0.7 TINOGARD TT Solid 0.1 0.1 DIETHYL CITRATE Liquid 0.1 0.1 Sum 100.0 100.0 100.0 Absolutes 2.3 5.2 0.0 Absolutes and Al ingredients 20.9 47.5 0.0 A2 ingredients 17.2 32.8 5.0 Sum Absolutes, Al and A2

[0229] 38.1 80.3 5.0 ingredients

[0230] Polar solvent 8.8 19.7 0.1

[0231] Turbid

[0232] solution Clear Clear Comments

[0233] with solution solution precipitate

[0234] The solution remains Mix of first and second parts clear over a 24 hours period

[0235] Additional polar solvent required 16 (TEC)

[0236] to solubilize the complete perfume 4 (DPG)

[0237] Total polar solvent to solubilize

[0238] 24.0

[0239] the complete perfume

[0240] Total polar solvent in the mix of

[0241] the first and second part (q.s.p. 8.8

[0242] 100%)

[0243] Absolute and Al ingredients to

[0244] 0.9 2.4

[0245]

[0246] polar solvent ratioAs apparent from Table 3 solubilizing full perfume A requires 20 wt.% of additional solvents, one of these solvents being petrochemical dipropylene glycol (at 4 wt.%) and the other being natural triethyl citrate (TEC) and 1,3 -butanediol. This makes 24 wt.% polar solvents in total in 100 wt.% of complete perfume oil. Conversely, splitting this perfume into first and second parts requires only 8.8 wt.% of natural TEC and no dipropylene glycol DPG. This result in saving of 63 % solvent and in a significant gain of naturality for the whole process.

[0247] Table 3 shows also that a clear, transparent first part comprising 47.5 wt.% of difficult to solubilize perfumery ingredients can be obtained. This first part, as well as the second part remain homogeneous and transparent when submitted to a temperature of -11°C (minus 11 °C) for 48 hours, 5°C for 2 weeks and 50 °C for 2 weeks. They are stable and can be stored for 24 months at a temperature of from 10°C to 25 °C before further use. Furthermore, both first and second parts can be diluted into a hydro-alcoholic medium in which both parts are mutually soluble.

[0248] Example 2, Preparation of a perfume oil comprising 4,7 wt. % of absolutes

[0249] In this example, a perfume oil composition 2 is prepared by mixing the perfume ingredients and solvents shown in Table 4. The percentages of the ingredients and solvents are also reported in Table 4. The fourth column shows the composition of the perfume oil composition displaying solubility issues (comparative example), while the fifth and sixth columns show the composition of both first and second oil parts after splitting according to the present invention. The first part to second part weight ratio is 0.28.

[0250] Table 4. Solubility of full perfume composition 2 and of its first part (22 wt.% of the perfume oil) of the complete perfume and second part (78 wt.% of the perfume oil).

[0251] Physical Complete First Second Perfumery Ingredient ClogP state at perfume Part Part

[0252] 25 °C [wt.%] [wt.%] [wt.%] Tonka Bean resinoid Solid 0.2 0.9

[0253] VANILLIN 1.28 Solid 1.1 5.0

[0254] Cocoa butter Solid 2.2 10.0

[0255] Cistus resinoid Solid 1.5 6.8

[0256] Carboresin Solid 0.8 3.6 DIPROPYLENE GLYCOL -0.69 Liquid 16.0 72.8 UNDECALACTONE DELTA 2.92 Liquid 0.2 0.9 HABANOLIDE 4.86 Liquid 9.3 11.9 ALDEHYDE C 12 MN A PURE 5.07 Liquid 2.0 2.6 Cedar oil Liquid 2.2 2.8 SYLVAMBER 4.85 Liquid 20.0 25.6

[0257]

[0258] ETHYLENE BRASSYLATE 3.02 Liquid 12.0 15.4MOXALONE 5.22 Liquid 6.0 7.7 CEDRYL METHYL ETHER 5.29 Liquid 20.0 25.7 Olibanum oil Liquid 2.2 2.8 IRISONE ALPHA 3.71 Liquid 1.3 1.7 Patchouli oil Liquid 3.0 3.8

[0259] Sum 100.0 100.0 100.0 Absolutes 4.7 17.7 0.0 Absolutes and Al ingredients 5.8 26.3 0.0

[0260] A2 ingredients 0.2 0.9 0.0

[0261] Sum Absolutes, Al and A2

[0262] 6.0 27.2 0.0 ingredients

[0263] Polar solvent 16.0 72.8 0.0

[0264] Turbid

[0265] solution Clear Clear Comments

[0266] with solution solution precipitate

[0267] The solution remains Mix of first and second parts clear over a 24 hours period

[0268] Additional polar solvent required to

[0269] 28 (DPG)

[0270] solubilize the complete perfume

[0271] Total polar solvent to solubilize the

[0272] 34.4

[0273] complete perfume (q.s.p. 100%)

[0274] Total polar solvent in the mix of the

[0275] 16.0

[0276] first and second part (q.s.p. 100%)

[0277] Absolute and Al ingredients to

[0278] 0.17 0.36

[0279]

[0280] polar solvent ratio

[0281] As apparent from Table 4, solubilizing perfume oil 2 requires an additional amount of 28 wt.% of dipropylene glycol (DPG). This makes 34.4 wt.% polar solvent in total in 100 wt.% of complete perfume oil. The main issue is the solubilisation of the Cocoa butter. Splitting the perfume oil into first and second parts allows reduction of the amount of solvent to 16 wt.%. This corresponds to a reduction of 54 wt.% of the required solvent.

[0282] Table 4 shows also that a clear, transparent first part comprising 26.3 wt.% of difficult to dissolve absolute and Al perfumery ingredients can be obtained. This first part, as well as the second part remain homogeneous and transparent when submitted to a temperature of -11°C (minus 11°C) for 48 hours, 5°C for 2 weeks and 50 °C for 2 weeks. They are stable and can be stored for 24 months at a temperature of from 10°C to 25 °C before further use. Furthermore, both first and second parts can be diluted into a hydro-alcoholic medium in which both parts are mutually soluble.

[0283] Example 3, Preparation of a perfume oil comprising 9,5 wt. % of absolutes and Al ingredientsIn this example, a perfume oil composition 3 is prepared by mixing the perfume ingredients and solvents shown in Table 5. The percentages of the ingredients and solvents are also reported in Table 5. The fourth column shows the composition of the full perfume composition showing solubility issues (comparative example), while the fifth and sixth columns show the composition of both first and second parts after splitting according to the present invention. The first part to second part weight ratio is 0.43.

[0284] Table 5. Solubility of full perfume composition 3 and of its first part (30 wt.% of the perfume oil) of the complete perfume and second part (70 wt.% of the full perfume).

[0285] Physical Complete First Second Perfumery Ingredient ClogP state at perfume Part Part

[0286] 25 °C [wt.%] [wt.%] [wt.%] HEDIONE HC 2.91 Liquid 6.0 20.0 BENZALDEHYDE 1.50 Liquid 0.5 1.7

[0287] COUMARIN NATURAL 1.41 Solid 3.0 10.0 AKIGALAWOOD Liquid 1.0 3.3

[0288] MAHONIAL 2.12 Liquid 1.0 3.3

[0289] Benzoin resinoid Solid 2.0 6.7

[0290] TROPIONAL 2.37 Liquid 1.0 3.3

[0291] TRIETHYL CITRATE 1.17 Liquid 5.0 16.6

[0292] DIPROPYLENE GLYCOL -0.69 Liquid 2.5 8.3

[0293] ETHYL LINALOOL 3.28 Liquid 2.0 6.7

[0294] HELIOTROPINE CRYSTALS 1.76 Solid 0.5 1.7

[0295] ETHYL MALTOL 0.63 Solid 2.0 6.7

[0296] BICYCLO NONALACTONE 1.19 Liquid 0.5 1.7

[0297] PRUNOLIDE 1.83 Liquid 1.0 3.3

[0298] VANILLIN NATURAL EXCLOVE 0.00 Solid 2.0 6.7

[0299] HELVETOLIDE 5.38 Liquid 9.0 12.9 AMBRETTOLIDE 5.42 Liquid 2.0 2.9 LINALYL ACETATE SYNTHETIC 3.69 Liquid 3.0 4.3 AMBROFIX 5.47 Solid 5.0 7.1 CITRONELLOL EXTRA 3.25 Liquid 2.0 2.9 ISORALDEINE 70 4.02 Liquid 12.0 17.1

[0300] IONONE BETA 3.77 Liquid 4.0 5.7

[0301] ISO E SUPER 4.85 Liquid 25.0 35.7 KEPHALIS 3.02 Liquid 1.0 1.4 METHYL CEDRYL KETONE 5.53 Liquid 4.0 5.7

[0302] Vetiver oil Solid 3.0 4.3

[0303] Sum 100.0 100.0 100.0 Absolutes 2.0 6.7 0.0 Absolutes and Al ingredients 9.5 31.8 0.0

[0304]

[0305] A2 ingredients 11.0 36.6 0.0Sum Absolutes, Al and A2

[0306] 20.5 68.4 0.0

[0307] ingredients

[0308] Polar solvent 7.5 24.9 0.0

[0309] Turbid

[0310] solution Clear Clear Comments

[0311] with solution solution precipitate

[0312] The solution

[0313] Mix of first and second parts remains clear over a

[0314] 24 hours period Additional polar solvent required

[0315] to solubilize the complete 28 (DPG)

[0316] perfume

[0317] Total polar solvent to solubilize

[0318] the complete perfume (q.s.p. 27.7

[0319] 100%)

[0320] Total polar solvent in the mix of

[0321] the first and second part (q.s.p. 7.5

[0322] 100%)

[0323] Absolute and Al ingredients to

[0324] 0.34 1.3

[0325]

[0326] polar solvent ratio

[0327] As apparent from Table 5, solubilizing full perfume 3 requires an additional amount of 28 wt.% or dipropylene glycol. This makes 27.7 wt.% polar solvent in total in 100 wt.% of complete perfume oil. Splitting the perfume oil into first and second parts allows reducing the amount of solvent to 7.5 wt.%. This corresponds to a reduction of 73 wt.% of the required solvent.

[0328] Table 5 shows also that a clear, transparent first part comprising 31.8 wt.% of difficult to solubilize perfumery ingredients can be obtained. This first part, as well as the second part remain homogeneous and transparent when submitted to a temperature of -11°C (minus 11 °C) for 48 hours, 5°C for 2 weeks and 50 °C for 2 weeks. They are stable and can be stored for 24 months at a temperature of from 10°C to 25 °C before further use. Furthermore, both first and second parts can be diluted into a hydro-alcoholic medium in which both parts are mutually soluble.

[0329] Example 4, Preparation of a perfume oil comprising 21,6 wt. % of absolutes and 15,4 wt.% Al ingredients

[0330] In this example, a perfume oil composition 4 is prepared by mixing the perfume ingredients and solvents shown in Table 5. The percentages of the ingredients and solvents are also reported in Table 6. The fourth column shows the composition of the full perfume composition showing solubility issues (comparative example), while the fifth and sixth columns show the composition of both first and second parts after splitting according to the present invention. The first part to second part weight ratio is 4.Table 6. Solubility of full perfume composition 4 and of its first part (80 wt.% of the perfume oil) of the complete perfume and second part (20 wt.% of the full perfume).

[0331] Physical Complete First Second Perfumery Ingredient ClogP state at perfume Part Part 25 °C [wt.%] [wt.%] [wt.%] Benzoin resinoid Solid 1.6 2.0 LINALOOL 2.75 Liquid 13.5 16.9 HEDIONE 2.91 Liquid 10 12.5 TRIETHYL CITRATE 1.17 Liquid 14 17.5

[0332] 1,3-BUTADIOL -0.73 Liquid 3.5 4.4

[0333] VANILLIN 1.28 Solid 9 11.3

[0334] Coffee absolute Solid 0.3 0.4

[0335] Peru balsam Solid 0.2 0.3 COUMARIN 1.41 Solid 6.4 8.0 DIPROPYLENE GLYCOL -0.69 Liquid 2 2.5

[0336] Tonka absolute Solid 19.5 24.2

[0337] Patchouli oil Liquid 5.5 27.5 Lavender oil Liquid 6.2 31.0 LINALOOL 2.75 Liquid 3.8 19.0 AMBRETTOLIDE 5.42 Solid 0.8 4.0 AMBROFIX 5.47 Liquid 0.8 4.0 GEORGYWOOD 4.85 Liquid 2.9 14.5 Sum 100.0 100.0 100.0 Absolutes 21.6 26.9 0.0 Absolutes and Al ingredients 37.0 46.2 0.0 A2 ingredients 13.5 16.9 19.0 Sum Absolutes, Al and A2

[0338] 50.5 63.1 19.0 ingredients

[0339] Polar solvent 19.5 24.4 0.0

[0340] Turbid

[0341] solution Clear Clear Comments

[0342] with solution solution precipitate

[0343] The solution remains Mix of first and second parts clear over a 24 hours period Additional polar solvent required to

[0344] 22 (DPG)

[0345] solubilize the complete perfume

[0346] Total polar solvent to solubilize the

[0347] 34.0

[0348] complete perfume (q.s.p. 100%)

[0349] Total polar solvent in the mix of the

[0350] 19.5

[0351] first and second part (q.s.p. 100%)

[0352] Absolute and Al ingredients to

[0353] 1.09 1.6

[0354]

[0355] polar solvent ratioAs apparent from Table 6, solubilizing full perfume 4 requires an additional amount of 22 wt.% or dipropylene glycol. This makes 34 wt.% polar solvent in total in 100 wt.% of complete perfume oil. The main issue is the solubilisation of the high level of absolutes, combined with the high level of Al ingredients. Splitting the perfume oil into first and second parts allows reducing the amount of solvent to 19.5 wt.%. This corresponds to a reduction of 43 wt.% of the required solvent. Table 5 shows also that a clear, transparent first part comprising 46.2 wt.% of difficult to solubilize perfumery ingredients can be obtained. This first part, as well as the second part remain homogeneous and transparent when submitted to a temperature of -11°C (minus 11 °C) for 48 hours, 5°C for 2 weeks and 50 °C for 2 weeks. They are stable and can be stored for 24 months at a temperature of from 10°C to 25 °C before further use. Furthermore, both first and second parts can be diluted into a hydro-alcoholic medium in which both parts are mutually soluble.

[0356] Example 5, Preparation of a fine fragrance as perfumed product

[0357] In first execution of the invention, a first fine fragrance has been obtained by performing the steps of: (1) preparing first and a second parts as described in Example 1 and (2) admixing 4.4 wt.% of first part, 4.6 g of second part to 90 wt.% of a mixture of 86 vol.% ethanol and 4 vol.% water. In second execution of the invention, a second fine fragrance has been obtained by performing the steps of: (1) preparing a first and a second parts as described in Example 1, and (2) admixing 4.4 wt.% of first part, 5.6 g of second part and, after 24 hours, (3) adding the mixture obtained in step 2) to 90 wt.% of a mixture of 86 vol.% ethanol and 4 vol.% water.

[0358] Both first and second fine fragrances showed identical performance and hedonic profiles.

Claims

Claims1. A perfume oil comprising, based on the total weight of the perfume oil:0.2 to 20 wt.% of at least one absolute;0 to 30 wt.% of a Group Al perfume ingredient;0 to 30 wt % of a Group A2 perfume ingredient;2 to 20 wt % of at least one polar solvent having a ClogP of 1.5 or less;20 to 80 wt.% of at least one Group B perfume ingredient;whereinGroup Al perfume ingredient is solid at 25 °C and has a ClogP of 3.0 or less;Group A2 perfume ingredient is liquid at 25 °C and has a ClogP of 3.0 or less;Group B ingredient has a ClogP that is greater than 3.0 and is not an absolute;the sum of the concentrations of the at least one absolute, Group Al, and Group A2 perfume ingredients is from 5 to 60 wt.%; the ratio of the sum of the concentrations of absolute and Group Al perfume ingredients to the at least one polar solvent is from 0.2 to 5; and wherein the perfume oil is not a formulation consisting of 3 wt % Bangalol ((E)-2-ethyl-4-(2, 2, 3 -trimethyl- 1-cy cl opent-3-enyl)but-2-en-l-ol); 4 wt % Benzoin Siam Resinoid 50 % in DPG; 3 wt % Bergamot oil; 2 wt % Cis 3 Hexenol 10% in DPG; 1 wt % Coumarin; 3 wt % Dihydromyrcenol; 16 wt % Ethylene Brassylate (1, 4-dioxacy cl oheptadecane-5, 17-dione); 1 wt % Heliotropin (benzo[d][l,3]dioxole-5-carbaldehyde); 18 wt % Lavender oil; 5 wt % Lyral (4-(4-hydroxy-4-methylpentyl)cyclohex-3-enecarbaldehyde); 10 wt % Methyl dihydrojasmonate (methyl 3-oxo-2-pentylcyclopentaneacetate); 12 wt % methyl ionone alpha iso; 3 wt % Oak Moss Synthetic 10 % in DPG; 3 wt % Olibanum resinoid; 3 wt % Patchouli light oil; 6 wt % Prunella; 4 wt % Silvanone (16-Hexadecanolide); and 3 wt % Vanillin.

2. The perfume oil according to claim 1, in the form of separate but functionally interacting first and second parts, wherein the first part comprises the absolute, optionally Group Al ingredients, polar solvent and optionally Group A2 ingredients, and the second part comprises Group B ingredients; wherein the ratio of the sum of the concentration of absolute and Group Al ingredients to the at least one polar solvent is from 0.2 to 5.

3. The perfume oil according to claim 2 wherein the first part comprises (by weight of the first part):0.5 to 25 wt.% of at least one absolute;0 to 50 wt.% of a Group Al perfume ingredient;0 to 50 wt % of a Group A2 perfume ingredient;5 to 75 wt % of at least one polar solvent having a ClogP of 1.5 or less;wherein the sum of the concentrations of the at least one absolute, Group Al perfume ingredients and Group A2 perfume ingredients is 25 to 95 wt.%; and wherein the second part comprises (by weight of the second part) at least 80 wt.% of Group B perfume ingredients.

4. The perfume oil according to any of claim 1 to 3, wherein the at least one absolute is selected from the group consisting of cistus absolute, hydrocarboresins, Myrrh resinoid, Oakwood absolute, Fir balsam, Bran absolute, Mate absolute, roasted Barley absolute, Benzoin resinoid, Akigalawood, Bergamot absolute, Labdanum resinoid, Galbanum resinoid, Olibanol, Tonka bean absolute, roasted Tonka bean absolute, Orris butter, Cocoa absolute, Coffee absolute and mixtures thereof.

5. The perfume oil according to any of claims 1 to 4, wherein the at least one polar solvent is selected from the group consisting of triethyl citrate, diethyl citrate, dipropylene glycol, propylene glycol, 1,3-propanediol, 1,2-propanediol, 1,3 -butanediol, 1,2-butanediol, 1,2-pentanediol, ethanol, glycerol carbonate, isopropylidene glycerol and mixtures thereof.

6. The perfume oil according to any of claims 1 to 5, wherein the at least one Group Al perfume ingredient is selected from the group consisting of 3- hydroxybutan-2-one; l-(4-methoxyphenyl)ethanone; 1 -phenylethanone; (E)-2- methoxy-4-(prop-l-en-l-yl)phenyl acetate; l-(2-pyrazinyl)ethanone; (1R,5S,E)- l,5-methylbicyclo[3.2.1]octan-8-one oxime; 8-methyl-l,5-benzodioxepin-3-one; 2-hydroxy-3-methylcyclopent-2-enone; 2H-chromen-2-one; 2-methoxy-4-methylphenol; p-cresol; 1,4-dimethoxybenzene; 2-ethyl-3-hydroxy-4H-pyran-4-one; 3-ethoxy-4-hydroxybenzaldehyde; methy-12,4-dihydroxy-3,6-dimethylbenzoate; benzo[d][l,3]dioxole-5-carbaldehyde; 4-(l,3-benzodioxol-5-yl)butan-2-one; 4,4a,5,9b-tetrahydroindeno[l,2-d][l,3]dioxine; IH-indole; 3- hydroxy-2-methyl-4H-pyran-4-one; 1 -(2 -naphthal enyl)-ethanone; 3 -methoxy-5 -methylphenol; 2 -phenyl acetic acid; 4-(4-hydroxyphenyl)butan-2-one; 2-ethoxy- 4-methylphenol; 4-hydroxy-3-methoxybenzaldehyde; 4-(l -3 -benzodi oxol-5-yl)-2-butanone; benzoic acid; and mixtures thereof.

7. The perfume oil according to any of claims 1 to 6, comprising 1 to 50 wt.%, more particularly from 5 to 50 wt.% of Group A2 perfume ingredients.

8. The perfume oil according to any of claims 1 to 7, wherein the at least one Group A2 perfume ingredient is selected from the group consisting of allyl 2-phenoxyacetate; N-ethyl-N-(m-tolyl)propionamide; hexan-l-ol; octan-l-ol; hexan-l-al; heptanal; octanal; pentyl formiate; 1-octene-3-ol; 4-m ethoxybenzyl acetate; 4-m ethoxybenzaldehyde; benzyl acetate; 4-phenylbutan-2-one; ethyl 6-acetoxyhexanoate; butyl acetate; 2-methylpropyl acetate; methyl 2-(3-oxo-2-pentylcyclopentyl)acetate; (E)-3-phenylprop-2-enenitrile; (E)-3-phenylprop-2-en-l-ol; (2E)-3-phenylprop-2-enal; 2-(2-mercaptopropan-2-yl)-5-methylcyclohexanone; (4-methylphenyl) acetate; 1 -methoxy -4-methylbenzene; 4-isopropylbenzaldehyde; (4-isopropylphenyl)methanol; 2.4-dimethylcyclohex-3-ene-l-carbaldehyde; 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene carbaldehyde; 6-pentyltetrahydro-2H-pyran-2-one; 5-hexyloxolan-2-one; 2-methoxy-4-propylphenol; methyl 2-(methylamino)benzoate; 2-methyl-l-phenylpropan-2-ol; 2-methyl-4-phenylbutan-2-ol; 2,6-dimethylheptan-2-ol; ethyl benzoate; ethyl butanoate; ethyl 2-methylpropanoate; 8-ethyl-l- oxaspiro[4.5]decan-2-one; ethyl 3-phenyloxirane-2-carboxylate; ethyl 2-hydroxybenzoate; 2-ethyl-3 -methylpyrazine; 4-allyl-2-methoxyphenol; 4-allyl-2-methoxyphenyl acetate; 3-(4-methoxyphenyl)-2-methylpropanal; methyl oct-2- ynoate; 4-isopropylcyclohexanol; ethyl 2-(2,4-dimethyl-l,3-dioxolan-2- yl)acetate; diethyl cyclohexane- 1.4-dicarboxylate; N,2-dimethyl-N- phenylbutanamide; (E)-3,7-dimethylocta-2,6-dien-l-ol; 2-(2-hydroxypropan-2-yl)-5-methylcyclohexanol; methyl 3 -oxo-2 -pentylcyclopentane acetate; heptanone-2; nonanal; (E)-hex-2-enal; (E)-hex-2-en-l-ol; (Z)-hex-3-en-l-yl acetate; undec-10-enenitrile; (Z)-hex-3-en-l-yl acetate; (Z)-hex-3-en-l-yl formate; 2-ethyl-4-hydroxy-5-methylfuran-3(2H)-one; 2-phenylpropanal; 4-formyl-2-methoxyphenyl 2-methylpropanoate; 2-methylpropyl 3-methoxypyrazine; (E)-2-methoxy-4-(prop-l-en-l-yl)phenol; 5-methyl-2-(prop-l-en-2-yl)cyclohexanol; (Z)-6-(pent-2-en-l-yl)tetrahydro-2H- pyran-2-one; (E)-6-(pent-3-en-l-yl)tetrahydro-2H-pyran-2-one; (Z)-hex-3-en-l-yl methyl carbonate; 2-(5-methyl-5-vinyltetrahydrofuran-2-yl)propan-2-ol; 3,7-dimethylocta-l,6- dien-3-ol; 2-(4-methylcyclohex-3-en-l-yl)propan-2-ol; (4E)-9-hydroxy-5,9- dimethyl-4-decenal; 4-(4-methoxyphenyl)butan-2-one; l-(p-tolyl)ethanone; methyl 2-aminobenzoate; methyl benzoate; methyl 3-phenylprop-2-enoate; (Z)-2-methyl-3-phenylacrylaldehyde; 5-hexyl-5-methyloxolan-2-one; 2-ethoxy-4-(methoxymethyl)phenol; (Z)-methyl 2-(3-oxo-2-(pent-2-en-l-yl)cyclopentyl)acetate; 8-methyl-l-oxaspiro[4.5]decan-2-one; methyl 2-methylbutanoate; methyl 2 -phenyl acetate; methyl 2-hydroxybenzoate; 4-methyl-5-pentyldihydrofuran-2(3H)-one; 3,7-dimethyl-2,6-octadien-l-ol; (2Z)-3,7-dimethylocta-2,6-dien-l-ol; l-(3-methylbenzofuran-2-yl)ethanone; (2E,6Z)-nona-2,6-dienal; (2Z,6E)-2,6-nonadien-l-ol; 5-pentyloxolan-2-one; (Z)-non-6-en-l-ol; 7-methoxy-3,7-dimethyloctan-2-ol; 5-heptyldihydrofuran-2(3H)-one; 2-(o-tolyl)ethanol; 2-(phenoxy)ethyl 2-methylpropanoate; 2-phenyl-ethanal; 2-phenylethyl acetate; 2-phenylethyl formate; 3-phenylpropanal; 3-phenylpropan-l-ol; 3-methylbut-2-en-l-yl acetate; 2-ethoxy-4-(isopropoxymethyl)phenol; (E)-5-methylheptan-3-one oxime; ethyl methyl phenyl glycidate; 2-(p-tolyl)acetaldehyde; 4-methyl-l-propan-2-ylcyclohex-3- en-l-ol; 2-(4-methyl-l -cyclohex-3 -enyl)propan-2-ol; 2-(4-methylcyclohex-3-en- l-yl)propan-2-ol; 4-methylbenzaldehyde; 2,4-dimethylcyclohex-3- enecarbaldehyde; 3 -phenylbutanal; 3-(benzo[d][l,3]dioxol-5-yl)-2-methylpropanal; 6-hexyltetrahydro-2H-pyran-2-one; and mixtures thereof.

9. A method of manufacturing a perfume oil as defined in claims 1 through 8, the method comprising the steps of:Providing first and second parts, wherein the first part comprises the absolute, optionally Group Al perfume ingredients, the polar solvent and optionally Group A2 perfume ingredients and the weight ratio of the sum of the absolute and Al perfume ingredients to the polar solvent is from 0.2 to 5; and the second part comprises the Group B ingredients;Dissolving the absolute and any Group Al ingredients in the first part; andBlending the first part in which absolute and optionally Group Al ingredients are dissolved with the second part to form the perfume oil.

10. A method according to claim 9 wherein the first part comprises, based on the total weight of the first part:0.5 to 25 wt.% of at least one absolute;0 to 50 wt.% of a Group Al perfume ingredient;0 to 50 wt. % of a Group A2 perfume ingredient;5 to 75 wt % of at least one polar solvent having a ClogP of 1.5 or less;wherein the second part comprises, based on the total weight of the second part, at least 80 wt % of Group B perfume ingredients; and wherein the weight ratio of the sum of the absolute and Group Al perfume ingredients to the polar solvent is from 0.2 to 5.

11. The use of a mixture of at least one polar solvent having a ClogP lower than 1.5 and optionally a Group A2 perfume ingredient for solubilizing absolutes and optionally Group Al ingredients in a perfume oil as defined in any of the claim 1 through 8, wherein the weight ratio of the sum of absolutes and Group Al ingredients to the polar solvent is from 0.2 to 5.

12. A consumer product comprising a perfume oil as defined in any of the claims 1 through 8.

13. The consumer product according to claim 12, selected from the group consisting of fine fragrance, eau de parfum, cologne, after shave, shave cream, shave gel, deodorant andantiperspirant in the form of spray, stick, roll-on, soap or powder, oral care product, toothpaste flavor, breath freshener, oral rinse, tooth whitener, denture adhesive, disinfectant, personal care, product, cleanser, soap, bar or liquid soap, body wash, body milk, body cream, hand sanitizer, hand wash, sunscreen product, lotion, shower gel, bath salt, liquid shampoo, solid shampoo, liquid hair care conditioner, solid hair care conditioner, hair rinse, hair refresher, hair fixative, hair styling or styling aid, hair dying product, and feminine hygiene product, skin care cream, lotion and serum, foundation, lipstick, mask, anti-ageing product, exfoliating scrub, foot cream, facial tissue, cleansing wipe, and talc, hard surface cleaner, all-purpose cleaner, dish wash liquid, automatic dish wash detergent and single dose detergent, toilet cleaner, rim block, wipe, foam, liquid refresher, air refresher, room deodorizer, candle, air scenting device, plug-in, aerosol, non-aerosol dispenser, weed, laundry detergent in powder, liquid, bar or single dose form, fabric softener in liquid or sheet, or powder form, drier sheet, fabric refresher, scent booster, and ironing water.

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