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WO2026012919A1 - Solid perfume compositions - Google Patents

Solid perfume compositions

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Publication number
WO2026012919A1
WO2026012919A1 PCT/EP2025/069104 EP2025069104W WO2026012919A1 WO 2026012919 A1 WO2026012919 A1 WO 2026012919A1 EP 2025069104 W EP2025069104 W EP 2025069104W WO 2026012919 A1 WO2026012919 A1 WO 2026012919A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
solid
perfume composition
wax
perfume
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/EP2025/069104
Other languages
French (fr)
Inventor
Julia VICQ
Madelyne PHAM
Aude DAUGERON-JOUAULT
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Firmenich SA
Original Assignee
Firmenich SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firmenich SA filed Critical Firmenich SA
Publication of WO2026012919A1 publication Critical patent/WO2026012919A1/en
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216Solid or semisolid forms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216Solid or semisolid forms
    • A61K8/0229Sticks
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00Formulations or additives for perfume preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • A61K2800/31Anhydrous
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/56Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Fats And Perfumes (AREA)

Abstract

The present invention relates to a solid perfume composition as well as consumer products comprising said solid perfume composition. Further, the present invention relates to the use of said solid perfume composition for enhancing and/or prolonging the perfume performance.

Description

SOLID PERFUME COMPOSITIONS
Technical Field
The present invention relates to a solid perfume composition as well as consumer products comprising said solid perfume composition. Further, the present invention relates to the use of said solid perfume composition for enhancing and/or prolonging the perfume performance.
Background
Microcapsules are employed to a large extent in the perfumery and flavouring industries. They constitute delivery systems for perfuming or flavouring ingredients and can be advantageously used in a very large number of applications. The encapsulation of active substances such as perfuming or flavouring ingredients provides at the same time a protection of the ingredients encapsulated therein against "aggressions" such as oxidation or moisture and allows, on the other hand, a certain control of the kinetics of flavour or fragrance release to induce sensory effects through sequential release.
In order to provide a consumer product with a certain flavor and fragrance, respectively, perfume preparations are added during the preparation of consumer products. These perfume preparations comprise perfume oil that may be present in free form, in encapsulated form, or in both free and encapsulated form. Such perfume preparations are commonly in liquid form, i.e. such compositions frequently contain large amounts of water, alcohols, or both. However, the use of liquid perfume compositions is not always expedient, in particular in case the use of microcapsules in solid form is desired that contain a water-soluble carrier material, as the presence of water/alcohol would compromise the stability of such microcapsules.
For example, WO 03/043728 and WO 2006/038134 describe solid microcapsules comprising perfume oil that is embedded within a water-soluble matrix. Said documents refer to microcapsules in solid form that can be prepared safely by spray drying in view of a reduced risk for flammability and explosion, respectively.
Moreover, the use of liquid perfume preparations is not expedient in case the preparation of a waterless or solid consumer product is desired. In view of the above, there is a need to provide perfume preparations that can comprise microcapsules with a water-soluble matrix, and that can be used for the preparation of waterless and solid consumer products.
Summary of the invention
In a first aspect, the present invention relates to a solid perfume composition comprising: a solid delivery system comprising a carrier material and a perfume oil, a lipid component, optionally, an additional benefit agent, and optionally, a free perfume oil.
In a second aspect, the present invention relates to a consumer product comprising said perfume composition.
In a third aspect, the present invention relates to the use of said solid perfume composition for enhancing and/or prolonging the perfume performance.
Detailed description
In a first aspect, the present invention relates to a solid perfume composition comprising: a solid delivery system comprising a carrier material and a perfume oil, a lipid component, optionally, an additional benefit agent, and optionally, a free perfume oil.
The solid perfume composition according to the invention comprises a solid delivery system comprising a carrier material and a perfume oil.
In a particular embodiment, the solid delivery system is a microcapsule. The microcapsule can have an average diameter size from 5 to 500 pm. The microcapsule can also have an average diameter size from 5 to 800 pm, for example from 50 to 300 pm.
In a particular embodiment, the solid delivery system is a microcapsule as described in WO 03/043728 or as described in WO 2006/038134. In a particular embodiment, the perfume oil comprised within the solid delivery system is dispersed or adsorbed within the carrier material.
In a particular embodiment, the perfume oil is dispersed within the carrier material. The carrier material can be selected from the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrines, natural or modified starch, vegetable gums, pectins, xanthanes, alginates, carragenans, cellulose derivatives, and mixtures thereof. Cellulose derivatives can be, for example, carboxymethyl cellulose, methylcellulose or hydroxyethylcellulose.
In a particular embodiment, the perfume oil is adsorbed within the carrier material. The carrier material can be selected from the group consisting of amorphous silica, precipitated silica, fumed silica, aluminosilicates, and mixtures thereof. Aluminosilicates can be zeolite or alumina.
In a particular embodiment, the carrier material comprises monomeric, oligomeric, or polymeric carrier materials, or any mixtures thereof.
In a particular embodiment, the monomeric carrier material is selected from the group consisting of glucose, fructose, mannose, galactose, arabinose, fucose, sorbitol, mannitol, and mixtures thereof.
In a particular embodiment, the oligomeric carrier material is selected from the group consisting of carbohydrates such as sucrose, lactose, raffinose, maltose, trehalose, and fructooligosaccharides.
In a particular embodiment, the polymeric carrier material is selected from the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrines, natural or modified starch such as aluminium octenylsuccinate starch, vegetable gums, pectins, xanthanes, alginates, carragenans, cellulose derivatives such as carboxymethyl cellulose, methylcellulose or hydroxyethylcellulose, morphous silica, precipitated silica, fumed silica, aluminosilicates such as zeolite, alumina, carbonate such as calcium carbonate, or any mixture thereof.
In a particular embodiment, the carrier material is selected from the group consisting of glucose, fructose, mannose, galactose, arabinose, fucose, sorbitol, mannitol, sucrose, lactose, raffinose, maltose, trehalose, fructo-oligosaccharides, polyvinyl acetate, polyvinyl alcohol, dextrines, natural or modified starch, vegetable gums, pectins, xanthanes, alginates, carragenans, cellulose and its derivatives, morphous silica, precipitated silica, fumed silica and aluminosilicates, and any mixture thereof. In a particular embodiment, the carrier material is water-soluble. In case of water-soluble carrier materials, the stability of the solid delivery system is compromised in case the solid perfume composition contains water. Water-solubility refers to the solubility in water at room temperature, i.e. at 21 °C.
In a particular embodiment, the solid delivery system further comprises an explosion suppressant and/or fireproofing agent. Under an “explosion suppressant and/or fireproofing agent”, an agent is understood that reduces the dust hazard explosion risk during the preparation of the solid delivery system by spray drying. Further details in this respect can be found in WO 03/043728 and WO 2006/038134, respectively.
In a particular embodiment, the explosion suppressant and/or fireproofing agent is selected from the group consisting of talc, sodium silicate, potassium silicate, sodium carbonate, sodium hydrogencarbonate, monoammonium phosphate or carbonate, diammonium phosphate, mono-, di-or trisodium phosphate, sodium hypophosphite, melamine cyanurate, chlorinated hydrocarbons, and mixtures thereof.
In a particular embodiment, the explosion suppressant and/or fireproofing agent is selected from the group of C1-C12 carboxylic acids, salts of C1-C12 carboxylic acids, and mixtures thereof.
In an embodiment, the carboxylic acid is selected from the group consisting of acetic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, caproic acid, citric acid, succinic acid, hydroxysuccinic acid, maleic acid, fumaric acid, oxylic acid, glyoxylic acid, adipic acid, lactic acid, lactic acid, tartric acid, salicylic acid, ascorbic acid, and mixtures thereof. The carboxylic acid salts can be the respective calcium or sodium salts of any of the aforementioned carboxylic acids.
In a particular embodiment, the explosion suppressant and/or fireproofing agent is selected from the group consisting of sodium silicate, potassium silicate, sodium carbonate, sodium hydrogencarbonate, monoammonium phosphate or carbonate, diammonium phosphate, mono-, di-or trisodium phosphate, sodium hypophosphite, melamine cyanurate, chlorinated hydrocarbons, C1-C12 carboxylic acids, salts of C1-C12 carboxylic acids, and mixtures thereof.
The explosion suppressant and/or fireproofing agent can be present in an amount of from 5 wt.% to 90 wt.% based on the total dry weight of the solid delivery system, preferably from 5 wt.% to 15 wt.%. The explosion suppressant and/or fireproofing agent can also be present in an amount of from 0.5 wt.% to 80 wt.% based on the total dry weight of the solid delivery system.
In a particular embodiment, the solid delivery system comprises the perfume oil in an amount of from 1 wt.% to 80 wt.% based on the total dry weight of the solid delivery system, preferably from 1 wt.% to 50 wt.%. Alternatively, the solid delivery system comprises the perfume oil in an amount of from 5 wt.% to 70 wt.% based on the total dry weight of the solid delivery system.
In a particular embodiment, the solid delivery system comprises the perfume oil in an amount of from 30 wt.% to 50 wt.% based on the total dry weight of the solid delivery system, preferably from 40 wt.% to 50 wt.%, more preferably from 45 wt.% to 50 wt.%.
By “perfume” (or also “perfume oil”) what is meant here is an ingredient or a composition that is a liquid at about 20°C.
According to any one of the above embodiments said perfume oil can be a perfuming ingredient alone or a mixture of ingredients in the form of a perfuming composition. As a “perfuming ingredient” it is meant here a compound, which is used for the primary purpose of conferring or modulating an odor. In other words such an ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to at least impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor. For the purpose of the present invention, perfume oil also includes a combination of perfuming ingredients with substances which together improve, enhance or modify the delivery of the perfuming ingredients, such as perfume precursors, modulators, emulsions or dispersions, as well as combinations which impart an additional benefit beyond that of modifying or imparting an odor, such as long-lastingness, blooming, malodor counteraction, antimicrobial effect, microbial stability, pest control.
The nature and type of the perfuming ingredients present in the oil phase do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect. In general terms, these perfuming ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfurous heterocyclic compounds and essential oils (for example Thyme oil), and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. In particular one may cite perfuming ingredients which are commonly used in perfume formulations, such as:
- Aldehydic ingredients: decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal, nonanal and/or nonenal;
- Aromatic-herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5- methyltricyclo[6.2.1 ,02 7]undecan-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4,4- dimethyl-1 ,3-oxathiane, 2,2,7/8,9/10-tetramethylspiro[5.5]undec-8-en-1-one, menthol and/or alpha-pinene;
- Balsamic ingredients: coumarin, ethylvanillin and/or vanillin;
- Citrus ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, 1-p-menthen-8-yl acetate and/or 1 ,4(8)-p-menthadiene;
- Floral ingredients: methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4- tert-butylphenyl)-2-methylpropanal, hexylcinnamic aldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta ionone, methyl 2- (methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2- one, (1 E)-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, 3-(3,3/1 ,1-dimethyl-5-indanyl)propanal, 2,5-dimethyl-2-indanmethanol, 2, 6, 6-trimethyl-3-cyclohexene-1 -carboxylate, 3-(4,4- dimethyl-1-cyclohexen-1-yl)propanal, hexyl salicylate, 3,7-dimethyl-1 ,6-nonadien-3-ol,
3-(4-isopropylphenyl)-2-methylpropanal, verdyl acetate, geraniol, p-menth-1-en-8-ol,
4-(1 ,1-dimethylethyl)-1-cyclohexyle acetate, 1 ,1-dimethyl-2-phenylethyl acetate, 4- cyclohexyl-2-methyl-2-butanol, amyl salicylate , high cis methyl dihydrojasmonate, 3- methyl-5-phenyl-1-pentanol, verdyl proprionate, geranyl acetate, tetrahydro linalool, cis-7-p-menthanol, propyl (S)-2-(1 ,1-dimethylpropoxy)propanoate, 2- methoxynaphthalene, 2, 2, 2-trichloro-1 -phenylethyl acetate, 4/3-(4-hydroxy-4- methylpentyl)-3-cyclohexene-1-carbaldehyde, amylcinnamic aldehyde, 8-decen-5- olide, 4-phenyl-2-butanone, isononyle acetate, 4-(1 , 1 -dimethylethyl)-1 -cyclohexyl acetate, verdyl isobutyrate and/or mixture of methylionones isomers;
- Fruity ingredients: gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2- methyl-4-propyl-1 ,3-oxathiane, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2- phenoxyethyl isobutyrate, ethyl 2-methyl-1 ,3-dioxolane-2-acetate, diethyl 1 ,4- cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, 1-[3,3- dimethylcyclohexyl]ethyl [3-ethyl-2-oxiranyl]acetate and/or diethyl 1 ,4-cyclohexane dicarboxylate; - Green ingredients: 2-methyl-3-hexanone (E)-oxime, 2,4-dimethyl-3-cyclohexene-1- carbaldehyde, 2-tert-butyl-1 -cyclohexyl acetate, styrallyl acetate, allyl (2- methylbutoxy)acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z)-3-hexen-1-ol and/or 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one;
- Musk ingredients: 1 ,4-dioxa-5,17-cycloheptadecanedione, (Z)-4-cyclopentadecen-1- one, 3-methylcyclopentadecanone, 1-oxa-12-cyclohexadecen-2-one, 1-oxa-13- cyclohexadecen-2-one, (9Z)-9-cycloheptadecen-1-one, 2-{(1 S)-1 -[(1 R)-3,3- dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3-methyl-5-cyclopentadecen-1 - one, 4,6,6,7,8,8-hexamethyl-1 ,3,4,6,7,8-hexahydrocyclopenta[g]isochromene, (1 S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propanoate, oxacyclohexadecan-2-one and/or (1 S,1 'R)-[1 -(3',3'-dimethyl-1 cyclohexyl)ethoxycarbonyl]methyl propanoate;
- Woody ingredients: 1-[(1 RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3-dimethyl-
5-[(1 R)-2,2,3-trimethyl-3-cyclopenten-1 -yl]-4-penten-2-ol, 3,4'-dimethylspiro[oxirane- 2,9'-tricyclo[6.2.1 ,02 7]undec[4]ene, (1 -ethoxyethoxy)cyclododecane, 2,2,9,11- tetramethylspiro[5.5]undec-8-en-1-yl acetate, 1 -(octa hydro-2, 3,8, 8-tetramethyl-2- naphtalenyl)-1 -ethanone, patchouli oil, terpenes fractions of patchouli oil, Clearwood®, (1 'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-2-buten-1-ol, 2-ethyl-4-(2,2,3- trimethyl-3-cyclopenten-1-yl)-2-buten-1-ol, methyl cedryl ketone, 5-(2,2,3-trimethyl-3- cyclopentenyl)-3-methylpentan-2-ol, 1 -(2,3,8,8-tetramethyl-1 ,2,3,4,6,7,8,8a- octahydronaphthalen-2-yl)ethan-1-one and/or isobornyl acetate;
- Other ingredients (e.g. amber, powdery spicy or watery): dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,1-b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, clove oil, 3-(1 ,3-benzodioxol-5-yl)-2- methylpropanal, 7-methyl-2H-1 ,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl- 1 ,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1- thia-4-azaspiro[4.4]nonane and/or 3-(3-isopropyl-1-phenyl)butanal.
It is also understood that said ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds also known as properfume or profragrance. Non-limiting examples of suitable properfumes may include 4-(dodecylthio)-4- (2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-1- cyclohexen-1-yl)-2-butanone, 3-(dodecylthio)-1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1- butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta- 2,6-dien-1-yl oxo(phenyl)acetate, (Z)-hex-3-en-1-yl oxo(phenyl)acetate, 3,7-dimethyl-2,6- octadien-1-yl hexadecanoate, bis(3,7-dimethylocta-2,6-dien-1-yl) succinate, (2-((2- methylundec-1-en-1-yl)oxy)ethyl)benzene, 1-methoxy-4-(3-methyl-4-phenethoxybut-3-en-1- yl)benzene, (3-methyl-4-phenethoxybut-3-en-1-yl)benzene, 1-(((Z)-hex-3-en-1-yl)oxy)-2- methylundec-1-ene, (2-((2-methylundec-1-en-1-yl)oxy)ethoxy)benzene, 2-methyl-1-(octan-3- yloxy)undec-1 -ene, 1 -methoxy-4-(1 -phenethoxyprop-1 -en-2-yl)benzene, 1 -methyl-4-(1 - phenethoxyprop-1 -en-2-yl)benzene, 2-(1 -phenethoxyprop-1 -en-2-yl)naphthalene, (2- phenethoxyvinyl)benzene, 2-(1-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-2-yl)naphthalene, (2-((2-pentylcyclopentylidene)methoxy)ethyl)benzene, 4-allyl-2-methoxy-1-((2-methoxy-2- phenylvinyl)oxy)benzene, (2-((2-heptylcyclopentylidene)methoxy)ethyl)benzene, 1 -isopropyl- 4-methyl-2-((2-pentylcyclopentylidene)methoxy)benzene, 2-methoxy-1-((2- pentylcyclopentylidene)methoxy)-4-propylbenzene, 3-methoxy-4-((2-methoxy-2- phenylvinyl)oxy)benzaldehyde, 4-((2-(hexyloxy)-2-phenylvinyl)oxy)-3-methoxybenzaldehyde or a mixture thereof.
The perfuming ingredients may be dissolved in a solvent of current use in the perfume industry. The solvent is preferably not an alcohol. Examples of such solvents are diethyl phthalate, isopropyl myristate, Abalyn® (rosin resins, available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes, or isoparaffins. Preferably, the solvent is very hydrophobic and highly sterically hindered, like for example Abalyn® or benzyl benzoate. Preferably the perfume comprises less than 30% of solvent. More preferably the perfume comprises less than 20% and even more preferably less than 10% of solvent, all these percentages being defined by weight relative to the total weight of the perfume. Most preferably, the perfume is essentially free of solvent.
Preferred perfuming ingredients are those having a high steric hindrance and in particular those from one of the following groups:
Group 1 : perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched Ci to C4 alkyl or alkenyl substituent;
Group 2: perfuming ingredients comprising a cyclopentane, cyclopentene, cyclopentanone or cyclo pente none ring substituted with at least one linear or branched C4 to C8 alkyl or alkenyl substituent;
Group 3: perfuming ingredients comprising a phenyl ring or perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched C5 to C8 alkyl or alkenyl substituent or with at least one phenyl substituent and optionally one or more linear or branched Ci to C3 alkyl or alkenyl substituents;
Group 4: perfuming ingredients comprising at least two fused or linked Cs and/or C8 rings; Group 5: perfuming ingredients comprising a camphor-like ring structure;
Group 6: perfuming ingredients comprising at least one C7 to C2o ring structure; Group 7: perfuming ingredients having a logP value above 3.5 and comprising at least one tert-butyl or at least one trichloromethyl substitutent;
Examples of ingredients from each of these groups are:
Group 1 : 2,4-dimethyl-3-cyclohexene-1-carbaldehyde (origin: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2,2-dimethyl-6-methylene-1- cyclohexanecarboxylate (origin: Firmenich SA, Geneva, Switzerland), nerone, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylate, rose oxide, (S)-1 ,8-p-menthadiene-7-ol (origin: Firmenich SA, Geneva, Switzerland), 1-p-menthene-4-ol, (1 RS,3RS,4SR)-3-p-mentanyl acetate, (1 R,2S,4R)- 4,6,6-trimethyl-bicyclo[3,1 ,1]heptan-2-ol, tetrahydro-4-methyl-2-phenyl-2H-pyran (origin: Firmenich SA, Geneva, Switzerland), cyclohexyl acetate, cyclanol acetate, 1 ,4- cyclohexane diethyldicarboxylate (origin: Firmenich SA, Geneva, Switzerland), (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (origin: Firmenich SA, Geneva, Switzerland), ((6R)-perhydro-3,6-dimethyl-benzo[B]furan-2-one (origin: Firmenich SA, Geneva, Switzerland), 2,4,6-trimethyl-4-phenyl-1 ,3-dioxane, 2,4,6- trimethyl-3-cyclohexene-1-carbaldehyde;
Group 2: (E)-3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (origin: Givaudan SA, Vernier, Switzerland), (1 'R,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'- yl)-2-buten-1-ol (origin: Firmenich SA, Geneva, Switzerland), (1'R,E)-3,3-dimethyl-5- (2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol (origin: Firmenich SA, Geneva, Switzerland), 2-heptylcyclopentanone, methyl-cis-3-oxo-2-pentyl-1 -cyclopentane acetate (origin: Firmenich SA, Geneva, Switzerland), 2, 2, 5-trimethyl-5-pentyl-1 -cyclopentanone (origin: Firmenich SA, Geneva, Switzerland), 3,3-dimethyl-5-(2,2,3-trimethyl-3- cyclopenten-1-yl)-4-penten-2-ol (origin: Firmenich SA, Geneva, Switzerland), 3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl)-2-pentanol (origin, Givaudan SA, Vernier, Switzerland);
Group 3: damascenes, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one (origin: Firmenich SA, Geneva, Switzerland), (1'R)-2-[2-(4'-methyl-3'-cyclohexen-1'- yl)propyl]cyclopentanone, alpha-ionone, beta-ionone, damascenone, mixture of 1-(5,5- dimethyl-1-cyclohexen-1-yl)-4-penten-1-one and 1-(3,3-dimethyl-1-cyclohexen-1-yl)-4- penten-1-one (origin: Firmenich SA, Geneva, Switzerland), 1-(2,6,6-trimethyl-1- cyclohexen-1-yl)-2-buten-1-one (origin: Firmenich SA, Geneva, Switzerland), (1S,1'R)-[1- (3',3'-Dimethyl-1'-cyclohexyl)ethoxycarbonyl]methyl propanoate (origin: Firmenich SA, Geneva, Switzerland), 2-tert-butyl-1 -cyclohexyl acetate (origin: International Flavors and Fragrances, USA), 1-(2,2,3,6-tetramethyl-cyclohexyl)-3-hexanol (origin: Firmenich SA, Geneva, Switzerland), trans-1-(2,2,6-trimethyl-1-cyclohexyl)-3-hexanol (origin: Firmenich SA, Geneva, Switzerland), (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2- one, terpenyl isobutyrate, 4-(1 ,1 -dimethylethyl)- 1 -cyclohexyl acetate (origin: Firmenich SA, Geneva, Switzerland), 8-methoxy-1-p-menthene, (1 S,1 'R)-2-[1 -(3',3'-dimethyl-1 '- cyclohexyl) ethoxy]-2-methylpropyl propanoate (origin: Firmenich SA, Geneva, Switzerland), para tert-butylcyclohexanone, menthenethiol, 1-methyl-4-(4-methyl-3- pentenyl)-3-cyclohexene-1-carbaldehyde, allyl cyclohexylpropionate, cyclohexyl salicylate, 2-methoxy-4-methylphenyl methyl carbonate, ethyl 2-methoxy-4-methylphenyl carbonate, 4-ethyl-2-methoxyphenyl methyl carbonate;
Group 4: Methyl cedryl ketone (origin: International Flavors and Fragrances, USA), a mixture of (1 RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.02 6]dec-3-en-8-yl 2-methylpropanoate and (1 RS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1 ,026]dec-4-en-8-yl 2-methylpropanoate, vetyverol, vetyverone, 1 -(octahydro-2, 3, 8, 8-tetramethyl-2-naphtalenyl)-1 -ethanone (origin: International Flavors and Fragrances, USA), (5RS,9RS,10SR)-2,6,9,10- tetramethyl-1-oxaspiro[4.5]deca-3,6-diene and the (5RS,9SR,10RS) isomer, 6-ethyl- 2,10,10-trimethyl-1-oxaspiro[4.5]deca-3,6-diene, 1 ,2,3,5,6,7-hexahydro-1 ,1 ,2,3,3- pentamethyl-4-indenone (origin: International Flavors and Fragrances, USA), a mixture of 3-(3,3-dimethyl-5-indanyl)propanal and 3-(1 ,1-dimethyl-5-indanyl)propanal (origin: Firmenich SA, Geneva, Switzerland), 3',4-dimethyl-tricyclo[6.2.1.0(2,7)]undec-4-ene-9- spiro-2'-oxirane (origin: Firmenich SA, Geneva, Switzerland), 9/10-ethyldiene-3- oxatricyclo[6.2.1 ,0(2,7)]undecane, (perhydro-5,5,8A-trimethyl-2-naphthalenyl acetate (origin: Firmenich SA, Geneva, Switzerland), octalynol, (dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,1-b]furan, origin: Firmenich SA, Geneva, Switzerland), tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl acetate and tricyclo[5.2.1 ,0(2,6)]dec-4-en-8-yl acetate as well as tricyclo[5.2.1.0(2,6)]dec-3-en-8-yl propanoate and tricyclo[5.2.1.0(2,6)]dec-4- en-8-yl propanoate, (+)-(1S,2S,3S)-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-spiro-2'- cyclohexen-4'-one;
Group 5: camphor, borneol, isobornyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5- ene-2-carbaldehyde, pinene, camphene, 8-methoxycedrane, (8-methoxy-2,6,6,8- tetramethyl-tricyclo[5.3.1.0(1 ,5)]undecane (origin: Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, mixture of 9-ethylidene-3-oxatricyclo[6.2.1.0(2, 7)]undecan-4- one and 10-ethylidene-3-oxatricyclo[6.2.1.027]undecan-4-one (origin: Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (origin: Firmenich SA, Geneva, Switzerland);
Group 6: (trimethyl-13-oxabicyclo-[10.1 ,0]-trideca-4,8-diene (origin: Firmenich SA, Geneva, Switzerland), 9-hexadecen-16-olide (origin: Firmenich SA, Geneva, Switzerland), pentadecenolide (origin: Firmenich SA, Geneva, Switzerland), 3-methyl- (4/5)-cyclopentadecenone .(origin: Firmenich SA, Geneva, Switzerland), 3- methylcyclopentadecanone (origin: Firmenich SA, Geneva, Switzerland), pentadecanolide (origin: Firmenich SA, Geneva, Switzerland), cyclopentadecanone (origin: Firmenich SA, Geneva, Switzerland), 1-ethoxyethoxy)cyclododecane (origin: Firmenich SA, Geneva, Switzerland), 1 ,4-dioxacycloheptadecane-5, 17-dione, 4,8- cyclododecadien-1-one;
Group 7: (+-)-2-methyl-3-[4-(2-methyl-2-propanyl)phenyl]propanal (origin: Givaudan SA, Vernier, Switzerland), 2, 2, 2-trichloro-1 -phenylethyl acetate.
Preferably, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from Groups 1 to 7, as defined above. More preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3 to 7, as defined above. Most preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3, 4, 6 or 7, as defined above.
According to another preferred embodiment, the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP above 3, preferably above 3.5 and even more preferably above 3.75.
According to a particular embodiment, the perfume used in the invention contains less than 10% of its own weight of primary alcohols, less than 15% of its own weight of secondary alcohols and less than 20% of its own weight of tertiary alcohols. Advantageously, the perfume used in the invention does not contain any primary alcohols and contains less than 15% of secondary and tertiary alcohols.
According to an embodiment, the oil phase (or the oil-based core) comprises:
- 25-100wt% of a perfume oil comprising at least 15wt% of high impact perfume raw materials having a Log T<-4, and
- 0-75wt% of a density balancing material having a density greater than 1 .07 g/cm3. “High impact perfume raw materials" should be understood as perfume raw materials having a LogT<-4. The odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charges and molecular mass. For convenience, the odor threshold concentration is presented as the common logarithm of the threshold concentration, i.e., Log [Threshold] (“LogT”).
A “density balancing material" should be understood as a material having a density greater than 1 .07 g/cm3 and having preferably low or no odor.
The odor threshold concentration of a perfuming compound is determined by using a gas chromatograph (“GO”). Specifically, the gas chromatograph is calibrated to determine the exact volume of the perfume oil ingredient injected by the syringe, the precise split ratio, and the hydrocarbon response using a hydrocarbon standard of known concentration and chainlength distribution. The air flow rate is accurately measured and, assuming the duration of a human inhalation to last 12 seconds, the sampled volume is calculated. Since the precise concentration at the detector at any point in time is known, the mass per volume inhaled is known and hence the concentration of the perfuming compound. To determine the threshold concentration, solutions are delivered to the sniff port at the back-calculated concentration. A panelist sniffs the GC effluent and identifies the retention time when odor is noticed. The average across all panelists determines the odor threshold concentration of the perfuming compound. The determination of odor threshold is described in more detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September,, 2008, pages 54-61.
The nature of high impact perfume raw materials having a Log T<-4 and density balancing material having a density greater than 1.07 g/cm3are described in WO2018115250, the content of which are included by reference.
According to an embodiment, the high impact perfume raw materials having a Log T<- 4 are selected from the group consisting of (+-)-1-methoxy-3-hexanethiol, 4-(4-hydroxy-1- phenyl)-2-butanone, 2-methoxy-4-(1-propenyl)-1 -phenyl acetate, pyrazobutyle, 3- propylphenol, 1-(3-methyl-1-benzofuran-2-yl)ethanone, 2-(3-phenylpropyl)pyridine, 1-(3, 3/5,5- dimethyl-1-cyclohexen-1-yl)-4-penten-1-one , 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1- one, a mixture comprising (3RS,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[b]furan-2- one and (3SR,3aRS,6SR,7ASR)-perhydro-3,6-dimethyl-benzo[b]furan-2-one, (+-)-1 -(5-ethyl- 5-methyl-1-cyclohexen-1-yl)-4-penten-1-one, (1'S,3'R)-1-methyl-2-[(1',2',2'- trimethylbicyclo[3.1 .0]hex-3'-yl)methyl]cyclopropyl}methanol, (+-)-3-mercaptohexyl acetate, (2E)-1-(2,6,6-trimethyl-1 ,3-cyclohexadien-1-yl)-2-buten-1-one, H-methyl-2h-1 ,5- benzodioxepin-3(4H)-one, (2E,6Z)-2,6-nonadien-1-ol, (4Z)-4-dodecenal, (+-)-4-hydroxy-2,5- dimethyl-3(2H)-furanone, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 3-methylindole, (+-)- perhydro-4alpha,8abeta-dimethyl-4a-naphthalenol, patchoulol, 2-methoxy-4-(1 - propenyl)phenol, mixture comprising (+-)-5,6-dihydro-4-methyl-2-phenyl-2H-pyran and tetrahydro-4-methylene-2-phenyl-2H-pyran, mixture comprising 4-methylene-2- phenyltetrahydro-2H-pyran and (+-)-4-methyl-2-phenyl-3,6-dihydro-2H-pyran, 4-hydroxy-3- methoxybenzaldehyde, nonylenic aldehyde, 2-methoxy-4-propylphenol, 3-methyl-5-phenyl-2- pentenenitrile, 1-(spiro[4.5]dec-6/7-en-7-yl)-4-penten-1-one(, 2-methoxynaphthalene, (-)- (3aR,5AS,9AS,9BR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 5-nonanolide, (3aR,5AS,9AS,9BR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, 7-isopropyl- 2H,4H-1 ,5-benzodioxepin-3-one, coumarin, 4-methylphenyl isobutyrate, (2E)-1 -(2,6,6- trimethyl-1 ,3-cyclohexadien-1-yl)-2-buten-1-one, beta, 2,2, 3-tetramethyl-delta-methylene-3- cyclopentene-1 -butanol, delta damascene ((2E)-1-[(1 RS,2SR)-2,6,6-trimethyl-3-cyclohexen- 1-yl]-2-buten-1-one), (+-)-3,6-dihydro-4,6-dimethyl-2-phenyl-2h-pyran, anisaldehyde, paracresol, 3-ethoxy-4-hydroxybenzaldehyde, methyl 2-aminobenzoate, ethyl methylphenylglycidate, octalactone gamma, ethyl 3-phenyl-2-propenoate, (-)-(2E)-2-ethyl-4- [(1 R)-2,2,3-trimethyl-3-cyclopenten-1 -yl]-2-buten-1-ol, paracresyl acetate, dodecalactone, tricyclone, (+)-(3R,5Z)-3-methyl-5-cyclopentadecen-1-one, undecalactone, (1 R,4R)-8- mercapto-3-p-menthanone, (3S,3AS,6R,7AR)-3,6-dimethylhexahydro-1-benzofuran-2(3H)- one, beta ionone, (+-)-6-pentyltetrahydro-2H-pyran-2-one, (3E,5Z)-1 ,3,5-undecatriene, 10- undecenal, (9E)-9-undecenal (9Z)-9-undecenal, (Z)-4-decenal, (+-)-ethyl 2- methylpentanoate, 1 ,2-diallyldisulfane, 2-tridecenenitrile, 3-tridecenenitrile, , (+-)-2-ethyl-4,4- dimethyl-1 ,3-oxathiane, (+)-(3R,5Z)-3-methyl-5-cyclopentadecen-1-one, 3-(4-tert- butylphenyl)propanal, allyl (cyclohexyloxy)acetate, methylnaphthylketone, (+-)-(4E)-3-methyl- 4-cyclopentadecen-1-one, (+-)-5E3-methyl-5-cyclopentadecen-1-one, cyclopropylmethyl 3- hexenoate, (4E)-4-methyl-5-(4-methylphenyl)-4-pentenal, (+-)-1-(5-propyl-1 ,3-benzodioxol-2- yl)ethanone, 4-methyl-2-pentylpyridine, (+-)-(E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1 - yl)-3-buten-2-one, (3aRS,5aSR,9aSR,9bRS)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1- b]furan, (2S,5R)-5-methyl-2-(2-propanyl)cyclohexanone oxime, 6-hexyltetrahydro-2H-pyran-
2-one, (+-)-3-(3-isopropyl-1-phenyl)butanal, methyl 2-(3-oxo-2-pentylcyclopentyl)acetate, 1- (2,6,6-trimethyl-1-cyclohex-2-enyl)pent-1-en-3-one, indol, 7-propyl-2H,4H-1 ,5-benzodioxepin-
3-one, ethyl praline, (4-methylphenoxy)acetaldehyde, ethyl tricyclo[5.2.1.0.2 6]decane-2- carboxylate, (+)-(1 'S,2S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2- ol, (4E)-3,3-dimethyl-5-[(1 R)-2,2,3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 8-isopropyl-6- methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, methylnonylacetaldehyde, 4-formyl-2- methoxyphenyl 2-methylpropanoate, (E)-4-decenal, (+-)-2-ethyl-4-(2,2,3-trimethyl-3- cyclopenten-1-yl)-2-buten-1-ol, (1 R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]oct-3-ene, (1 R,4R,5R)-4,7,7-trimethyl-6-thiabicyclo[3.2.1]octane, (-)-(3R)-3,7-dimethyl-1 ,6-octadien-3-ol, (E)-3-phenyl-2-propenenitrile, 4-methoxybenzyl acetate, (E)-3-methyl-5-(2,2,3-trimethyl-3- cyclopenten-1-yl)-4-penten-2-ol, allyl (2/3-methylbutoxy)acetate, (+-)-(2E)-1-(2,6,6-trimethyl- 2-cyclohexen-1-yl)-2-buten-1-one, (1E)-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1-penten-3-one, and mixtures thereof.
According to an embodiment, perfume raw materials having a Log T<-4 are chosen in the group consisting of aldehydes, ketones, alcohols, phenols, esters lactones, ethers, epoxydes, nitriles and mixtures thereof.
According to an embodiment, perfume raw materials having a Log T<-4 comprise at least one compound chosen in the group consisting of alcohols, phenols, esters lactones, ethers, epoxydes, nitriles and mixtures thereof, preferably in amount comprised between 20 and 70% by weight based on the total weight of the perfume raw materials having a Log T<-4.
According to an embodiment, perfume raw materials having a Log T<-4 comprise between 20 and 70% by weight of aldehydes, ketones, and mixtures thereof based on the total weight of the perfume raw materials having a Log T<-4. The remaining perfume raw materials contained in the oil-based core may have therefore a Log T>-4.
According to an embodiment, the perfume raw materials having a Log T>-4 are chosen in the group consisting of ethyl 2-methylbutyrate, (E)-3-phenyl-2-propenyl acetate, (+-)-6/8- sec-butylquinoline, (+-)-3-(1 ,3-benzodioxol-5-yl)-2-methylpropanal, verdyl propionate, 1- (octahydro-2, 3, 8, 8-tetramethyl-2-naphtalenyl)-1 -ethanone, methyl 2-((1 RS,2RS)-3-oxo-2- pentylcyclopentyl)acetate, (+-)-(E)-4-methyl-3-decen-5-ol, 2,4-dimethyl-3-cyclohexene-1 - carbaldehyde, 1 ,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, tetrahydro-4-methyl-2-(2-methyl-1- propenyl)-2H-pyran, dodecanal, 1-oxa-12/13-cyclohexadecen-2-one, (+-)-3-(4- isopropylphenyl)-2-methylpropanal, aldehyde C11 , (+-)-2,6-dimethyl-7-octen-2-ol, allyl 3- cyclohexylpropanoate, (Z)-3-hexenyl acetate, 5-methyl-2-(2-propanyl)cyclohexanone, allyl heptanoate, 2-(2-methyl-2-propanyl)cyclohexyl acetate, 1 ,1-dimethyl-2-phenylethyl butyrate, geranyl acetate, neryl acetate, (+-)-1 -phenylethyl acetate, 1 ,1-dimethyl-2-phenylethyl acetate, 3-methyl-2-butenyl acetate, ethyl 3-oxobutanoate, (2Z)-ethyl 3-hydroxy-2-butenoate, 8-p- menthanol, 8-p-menthanyl acetate, 1-p-menthanyl acetate, (+-)-2-(4-methyl-3-cyclohexen-1- yl)-2-propanyl acetate, (+-)-2-methylbutyl butanoate, 2-{(1 S)-1-[(1 R)-3,3- dimethylcyclohexyl]ethoxy}-2-oxoethyl propionate, 3,5,6-trimethyl-3-cyclohexene-1 - carbaldehyde, 2, 4, 6-trimethyl-3-cyclohexene-1 -carbaldehyde, 2-cyclohexylethyl acetate, octanal, ethyl butanoate, (+-)-(3E)-4-(2,6,6-trimethyl-1/2-cyclohexen-1-yl)-3-buten-2-one, 1- [(1 RS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 1 ,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, 1 ,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, ethyl hexanoate, undecanal, decanal, 2-phenylethyl acetate, (1S,2S,4S)-1 ,7,7-trimethylbicyclo[2.2.1]heptan-2-ol, (1S,2R,4S)-1 ,7,7- trimethylbicyclo[2.2.1]heptan-2-ol ), (+-)-3,7-dimethyl-3-octanol, 1-methyl-4-(2- propanylidene)cyclohexene, (+)-(R)-4-(2-methoxypropan-2-yl)-1 -methylcyclohex-1 -ene, verdyl acetate, (3R)-1-[(1 R,6S)-2,2,6-trimethylcyclohexyl]-3-hexanol, (3S)-1-[(1 R,6S)-2,2,6- trimethylcyclohexyl]-3-hexanol, (3R)-1-[(1S,6S)-2,2,6-trimethylcyclohexyl]-3-hexanol, (+)- (1 S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propanoate, and mixtures thereof.
According to an embodiment, the core comprises a perfume formulation comprising:
- 0 to 60 wt.% of a hydrophobic solvent (based on the total weight of the perfume formulation),
- 40 to 100 wt.% of a perfume oil (based on the total weight of the perfume formulation), wherein the perfume oil has at least two, preferably all of the following characteristics: o at least 35%, preferably at least 40%, preferably at least 50%, more preferably at least 60% of perfuming ingredients having a log P above 3, preferably above 3.5, o at least 20%, preferably at least 25%, preferably at least 30%, more preferably at least 40% of Bulky materials of groups 1 to 6, preferably 3 to 6 as herein defined and o at least 15%, preferably at least 20%, more preferably at least 25%, even more preferably at least 30% of high impact perfume materials having a Log T < -4, optionally, further hydrophobic active ingredients.
According to a particular embodiment, the hydrophobic solvent is a density balancing material preferably chosen in the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylate, benzyl cinnamate, and mixtures thereof.
In a particular embodiment, the solid delivery system has been prepared by spray drying.
In a particular embodiment, the solid delivery system has been prepared as described in WO 03/043728 or WO 2006/038134.
In a particular embodiment, the solid delivery system is comprised within the solid perfume composition in an amount of from 0.1 wt.% to 5 wt.%, based on the total weight of the solid perfume composition, preferably in an amount of from 0.5 wt.% to 2 wt.%, more preferably in an amount of 1 wt.%.
In a particular embodiment, the solid delivery system consists of a carrier material and a perfume oil.
According to the invention, the solid perfume composition comprises a lipid component. The lipid component allows suspending the solid delivery system in the perfume composition without bursting the solid delivery system. Moreover, the perfume oil does not leak from the solid delivery system, which allows the perfume oil to be released during the actual application as desired.
In a particular embodiment, the lipid component comprises a combination of oils, butters and waxes, preferably a combination of natural oils, butters and waxes. Preferably, the lipid component consists of a combination of oils, butters and waxes, preferably a combination of natural oils, butters and waxes.
In a particular embodiment, the butters are selected from the group consisting of Mangifera indica see butter, Garcinia indica Seed Butter, Mango butter, Kokum butter, cacao seed butter, shea butter, apricot butter, and any mixture thereof; and/or the oils are selected from the group consisting of Corylus avellana seed oil, Macadamia nut oil, Caprilic/Capric Triglycerides, Coco- caprylate/caprate, hazelnut oil, castor oil, camellia oil, sunflower seed oil, argan oil, sweet almond oil, jojoba seed oil, rice bran oil, apple seed oil, olea oil, moringa seed oil, plum oil, raspberry seed oil, avocado seed oil, camellia oil, baobab oil, and any mixture thereof; and/or the waxes are selected from the group consisting of Rice wax, Bees wax, candelilla wax, palm wax, coco wax, rapeseed wax, soy wax, carnauba wax, sunflower wax, apricot wax, floral wax such as Acacia Decurrens Flower Wax, Polianthes Tuberosa Flower Wax, Helichrysum Angustifolium Flower wax, Jasminum Officinale Flower Wax, Lavandula Angustifolia Flower Wax, Narcissus Poeticus Flower Wax, Cananga Odorata Flower Wax, Rosa Centifolia Flower Wax, Rosa Damascena Flower Wax, Marigold Floral Wax and any mixture thereof.
In a particular embodiment, the butters are selected from the group consisting of Mangifera indica see butter, Garcinia indica Seed Butter, Mango butter, Kokum butter, and any mixture thereof.
In a particular embodiment, the oils are selected from the group consisting of Corylus avellana seed oil, Macadamia nut oil, Caprilic/Capric Triglycerides, Coco-caprylate/caprate, hazelnut oil, and any mixture thereof.
In a particular embodiment, the waxes are selected from the group consisting of Rice wax, Bees wax, floral wax such as Acacia Decurrens Flower Wax, Polianthes Tuberosa Flower Wax, Helichrysum Angustifolium Flower wax, Jasminum Officinale Flower Wax, Lavandula Angustifolia Flower Wax, Narcissus Poeticus Flower Wax, Cananga Odorata Flower Wax, Rosa Centifolia Flower Wax, Rosa Damascena Flower Wax, Marigold Floral Wax and any mixture thereof.
In a particular embodiment, the solid perfume composition comprises the lipid component in an amount of from 25 wt.% to 95 wt.%, based on the total weight of the solid perfume composition, preferably from 25 wt.% to 70 wt.%. In a particular embodiment, the solid perfume composition comprises the butters in an amount of from 10 wt.% to 50 wt.%, based on the total weight of the solid perfume composition, preferably from 10 wt.% to 30 wt.%.
In a particular embodiment, the solid perfume composition comprises the oils in an amount of from 5 wt.% to 30 wt.%, based on the total weight of the solid perfume composition, preferably from 7 wt.% to 20 wt.%.
In a particular embodiment, the solid perfume composition comprises the waxes in an amount of from 10 wt.% to 40 wt.%, based on the total weight of the solid perfume composition, preferably from 10 wt.% to 15 wt.%.
In a particular embodiment, the solid perfume composition comprises perfume oil (total) in an amount of at least 15 wt.%, preferably at least 20 wt.%, more preferably at least 25 wt.% and even more preferably at least 30 wt.%, based on the total weight of the solid perfume composition. The reference to “total perfume oil” refers to both, the perfume oil being present in the solid delivery system and the optional free perfume oil. It is an advantage of the solid perfume composition according to the invention that large amounts of perfume oil can be incorporated therein.
In a particular embodiment, the solid perfume composition comprises perfume oil (total) in an amount of from 10 to 50 wt.%, preferably from 20 to 40 wt.%, more preferably from 25 to 35 wt.%, based on the total weight of the solid perfume composition
In a particular embodiment, the solid perfume composition comprises free perfume oil in an amount of from 10 wt.% to 40 wt.%, based on the total weight of the solid perfume composition, preferably from 25 wt.% to 35 wt.%., more preferably in an amount of 30 wt.%.
In a particular embodiment, the solid perfume composition comprises free perfume oil in an amount of from 2 wt.% to 40 wt.%, based on the total weight of the solid perfume composition, preferably from 5 wt.% to 35 wt.%.
In a particular embodiment, the solid perfume composition comprises encapsulated perfume oil, i.e. perfume oil being present in the solid delivery system, in an amount of from 0.1 wt.% to 10 wt.%, based on the total weight of the solid perfume composition, preferably from 0.1 wt.% to 5 wt.%., more preferably from 0.1 wt.% to 1 wt.%, most preferably from 0.2 wt.% to 0.5 wt.%. In a particular embodiment, the solid perfume composition comprises free perfume oil in an amount of from 2 wt.% to 40 wt.%, based on the total weight of the solid perfume composition, preferably from 5 wt.% to 35 wt.%, and the solid perfume composition comprises encapsulated perfume oil, i.e. perfume oil being present in the solid delivery system, in an amount of from 0.1 wt.% to 10 wt.%, based on the total weight of the solid perfume composition, preferably from 0.1 wt.% to 5 wt.%., more preferably from 0.1 wt.% to 1 wt.%, most preferably from 0.2 wt.% to 0.5 wt.%.
In a particular embodiment, the weight ratio of free perfume oil and encapsulated perfume oil (i.e. perfume oil being present in the solid delivery system) in the solid perfume composition is from 100:1 to 10:1 , preferably from 80:1 to 40:1 , more preferably from 70:1 to 60:1 , most preferably from 65:1 to 60:1.
In Examples 3 and 4 of the present patent application, it has been found that even low amounts of encapsulated perfume oil as compared to free perfume oil, i.e. even in case of a high weight ratio of free to encapsulated perfume oil, an enhanced fragrance intensity over a prolonged period of time could be perceived based on the presence of only little amounts of encapsulated perfume oil.
In a particular embodiment, the solid perfume composition does not comprise an aqueous and/or an alcoholic liquid, preferably the solid perfume composition does not comprise water and/or ethanol. The solid perfume composition thus can be waterless. The solid perfume composition according to the invention represents a performant alternative to common liquid and water-based perfume formulations and also allows the suspension of microcapsules having a water-soluble matrix material. Moreover, the solid perfume composition according to the invention is also suitable for the preparation of waterless and solid consumer products.
The solid perfume composition according to the invention may comprise further additional benefits agents.
In a particular embodiment, the additional benefit agent includes absorbing agents, antioxidants, vitamins, dyes, and sweeteners. Preferably, the additional benefit agent is an absorbing agent or an antioxidant. The adsorbing agent may be calcium carbonate, aluminium octenylsuccinate starch, or a mixture thereof. The antioxidant may be a tocopherol. In a particular embodiment, the solid perfume composition comprises the additional benefit agent in an amount of from 0.1 wt.% to 10 wt.%, based on the total weight of the solid perfume composition.
In a particular embodiment, the solid perfume composition comprises an adsorbing agent in an amount of from 0.1 wt.% to 10 wt.%, based on the total weight of the solid perfume composition.
In a particular embodiment, the solid perfume composition comprises an antioxidant in an amount of from 0.1 wt.% to 2 wt.%, based on the total weight of the solid perfume composition.
Another aspect of the present invention is a process for preparing a solid perfume composition comprising the steps of: heating at least one lipid component at a temperature T 1 greater than the melting point of the lipid component(s),
- optionally, adding a free oil and/or an additional benefit agent, preferably at a temperature T2<T 1 , and
- adding a delivery system comprising a carrier material and a perfume oil, at a temperature T3<T1 to obtain a solid perfume composition.
Another aspect of the present invention relates to a consumer product comprising the solid perfume composition according to the invention.
In a particular embodiment, the consumer product is a personal care or cosmetic product, such as a solid perfumed stick, perfumed balm, perfumed concrete, or monodose perfume.
In a particular embodiment, the consumer product is selected from the group consisting of a Cologne, an after-shave lotion, a soap, a bath or shower gel, a deodorant, a body lotion, a shampoo or another hair-care product, a detergent, a fabric softener, a household cleaner and a cleaning and deodorising block for toilet tanks.
In a particular embodiment, the consumer product is a solid and/or waterless personal care or cosmetic product. As discussed above, the solid perfume composition according to the invention is suitable for the preparation of solid and waterless consumer products.
In a particular embodiment, the consumer product is a solid perfumed stick or a waterless perfumed balm. Another aspect of the present invention relates to the use of a solid perfume composition according to the invention for enhancing and/or prolonging the perfume performance. The terms “enhancing and/or prolonging” refer to the fact that perfume is encapsulated in the solid delivery system, which allows for a controlled and prolonged release of the perfume oil as compared to a situation if the perfume oil was not encapsulated within the solid delivery system. In particular, the term “enhancing” describes that the perfume oil perception is not only prolonged but also enhanced by the presence of the encapsulated perfume oil.
In an embodiment, the terms “enhancing” and/or “prolonging” are fulfilled in case at least 50% preferably at least 60%, of panelists of a sensorial study perceive a higher perfume oil intensity after application of a consumer product comprising the solid perfume composition according to the invention as compared to the application of a corresponding consumer product comprising a corresponding perfume composition that, however, does not show encapsulated perfume oil and the solid delivery system, respectively. In an embodiment, this perceived higher perfume oil intensity is observed directly after application of a consumer product and/or up to 4 hours after application.
Examples
Example 1 - Preparation of a silky fragrance stick
A silky fragrance stick as defined in Table 1 has been prepared as follows: mixing all ingredients of part A under stirring and heating up to 80 °C until a homogenous liquid composition has been achieved;
- the composition thus achieved has been cooled down to 70 °C and part B as defined in Table 1 has been added under stirring;
- the composition thus achieved has been cooled down to 50 °C and part C as defined in Table 1 has been added under stirring;
- the composition thus obtained has then been poured into the packing and cooled down to room temperature.
Table 1. Composition of a silky fragrance stick
2) Kokum Butter, origin: HUILES BERTIN
3) Huile de noisette BIO 2D, origin: HUILES BERTIN
4) LABRAFAC CC, origin: GATTEFOSSE
5) CETIOL C5, origin: BASF
6) Nat Rice Bran Wax, origin: NATUROCHIM
7) Bees wax white, origin: HENRY LAMOTTE
8) origin: DSM-FIRMENICH
9) Calmaru SCS-M5, origin: SAKAI CHEMICAL
10) COVI-OX T90 EU, origin: BASF
11) Microcapsules A (see preparation protocol below)
Preparation of Microcapsules A:
An emulsion of the following composition was spray-dried in a spray-drier Buchi (origin: Switzerland) to obtain spray-dried granules having the following compositions:
Table 1a. Composition of the spray-dried Microcapsules A
Example 2 - Preparation of a perfumed balm
A perfumed balm as defined in Table 2 has been prepared as follows: - mixing all ingredients of part A under stirring and heating up to 80 °C until a homogenous liquid composition has been achieved;
- the composition thus achieved has been cooled down to 70 °C and part B as defined in Table 2 has been added under stirring;
- the composition thus achieved has been cooled down to 50 °C and part C as defined in Table 2 has been added under stirring;
- the composition thus obtained has then been poured into the packing and cooled down to room temperature.
Table 2. Composition of a perfumed balm
2) Kokum Butter, origin: HUILES BERTIN
3) Huile de noisette BIO 2D, origin: HUILES BERTIN
4) Macadamia nut oil, origin: NATUROCHIM
5) NEOBEE M5, origin: STEPAN COMPANY
6) Nat Rice Bran Wax, origin: NATUROCHIM
7) origin: DSM-FIRMENICH
8) 0905125 Agenaflo OS, origin: AGRANA
9) COVI-OX T90 EU, origin: BASF
10) Microcapsules A
Comparative examples 1 and 2
A silky fragrance stick as described in Example 1 has been prepared with the only difference that no fragrance capsules have been added (Comparative Example 1).
Likewise, a perfumed balm as described in Example 2 has been prepared with the only difference that no fragrance capsules have been added (Comparative Example 2).
Example 3 - Sensorial evaluation of the silky fragrance stick of Example 1 and Comparative Example 1
Eight panelists (n=8) evaluated the performance of the silky fragrance stick of Example 1 and that of Comparative Example 1. For this purpose, each panelist applied the silky fragrance stick of Example 1 on the one forearm and the silky fragrance stick of Comparative Example 1 on the other forearm. On each forearm, the respective fragrance stick was applied by conducting five circles on the skin with the respective stick.
The panelists were then asked to evaluate on which forearm the greatest perfume intensity was perceived, i.e. the panelists had to evaluate whether silky fragrance stick of Example 1 or that of Comparative Example 1 conferred a higher perfume intensity. This evaluation was performed at different time points: zero (directly after application), 30 minutes, 1 hour, 2 hours, and 4 hours. The results are shown in Table 3.
Table 3. Outcome of the sensorial evaluations
As shown in Table 3, at all time points the majority of panelists found that the silky fragrance stick of Example 1 confers a higher perfume intensity as compared to the fragrance stick of Comparative Example 1. This demonstrates that the fragrance capsules in Example 1 were successfully incorporated into a matrix that allows the fragrance capsules to exert its function with respect to perfume intensity enhancement and prolongation of perfume intensity, respectively.
Example 4 - Sensorial evaluation of the perfumed balm of Example 2 and Comparative Example 2
Nine panelists (n=9) evaluated the performance of the perfumed balm of Example 2 and that of Comparative Example 2. For this purpose, each panelist applied the perfumed balm of Example 2 on the one forearm and the perfumed balm of Comparative Example 2 on the other forearm. The respective perfumed balm was applied on each forearm by dipping a finger into the perfumed balm, conducting ten circles within the balm, and applying the balm on the skin by conducting five circles on the skin with the finger.
The panelists were then asked to evaluate on which forearm the greatest perfume intensity was perceived, i.e. the panelists had to evaluate whether the balm of Example 2 or that of Comparative Example 2 conferred a higher perfume intensity. This evaluation was performed at different time points: zero (directly after application), 30 minutes, 1 hour, 2 hours, and 4 hours. The results are shown in Table 4.
Table 4. Outcome of the sensorial evaluations
As shown in Table 4, at all time points the majority of panelists found that the balm of Example 2 confers a higher perfume intensity as compared to the balm of Comparative Example 2. This demonstrates that the fragrance capsules in Example 2 were successfully incorporated into a matrix that allows the fragrance capsules to exert its function with respect to perfume intensity enhancement and prolongation of perfume intensity, respectively.

Claims

1 . A solid perfume composition comprising: a solid delivery system comprising a carrier material and a perfume oil, a lipid component, optionally, an additional benefit agent, and optionally, a free perfume oil.
2. The solid perfume composition according to claim 1 , wherein the lipid component comprises a combination of oils, butters and waxes, preferably a combination of natural oils, butters and waxes.
3. The solid perfume composition according to claim 2, wherein the butters are selected from the group consisting of Mangifera indica see butter, Garcinia indica Seed Butter, Mango butter, Kokum butter, cacao seed butter, shea butter, apricot butter, and any mixture thereof; and/or the oils are selected from the group consisting of Corylus avellana seed oil, Macadamia nut oil, Caprilic/Capric Triglycerides, Coco- caprylate/caprate, hazelnut oil, castor oil, camellia oil, sunflower seed oil, argan oil, sweet almond oil, jojoba seed oil, rice bran oil, apple seed oil, olea oil, moringa seed oil, plum oil, raspberry seed oil, avocado seed oil, camellia oil, baobab oil, and any mixture thereof; and/or the waxes are selected from the group consisting of Rice wax, Bees wax, candelilla wax, palm wax, coco wax, rapeseed wax, soy wax, carnauba wax, sunflower wax, apricot wax, floral wax such as Acacia Decurrens Flower Wax, Polianthes Tuberosa Flower Wax, Helichrysum Angustifolium Flower wax, Jasminum Officinale Flower Wax, Lavandula Angustifolia Flower Wax, Narcissus Poeticus Flower Wax, Cananga Odorata Flower Wax, Rosa Centifolia Flower Wax, Rosa Damascena Flower Wax, Marigold Floral Waxand any mixture thereof.
4. The solid perfume composition according to any of the preceding claims, wherein the perfume oil comprised within the solid delivery system is dispersed or adsorbed within the carrier material.
5. The solid perfume composition according to any of the preceding claims, wherein the carrier material is selected from the group consisting of glucose, fructose, mannose, galactose, arabinose, fucose, sorbitol, mannitol, sucrose, lactose, raffinose, maltose, trehalose, fructo-oligosaccharides, polyvinyl acetate, polyvinyl alcohol, dextrines, natural or modified starch, vegetable gums, pectins, xanthanes, alginates, carragenans, cellulose and its derivatives, morphous silica, precipitated silica, fumed silica and aluminosilicates, and any mixture thereof.
6. The solid perfume composition according to any of the preceding claims, wherein the carrier material is water-soluble.
7. The solid perfume composition according to any of the preceding claims, wherein the solid delivery system is comprised within the solid perfume composition in an amount of from 0.1 wt.% to 5 wt.%, based on the total weight of the solid perfume composition.
8. The solid perfume composition according to any of the preceding claims, wherein the solid perfume composition comprises perfume oil (total) in an amount of at least 15 wt.%, preferably at least 20 wt.%, more preferably at least 25 wt.% and even more preferably at least 30 wt.%, based on the total weight of the solid perfume composition.
9. The solid perfume composition according to any of the preceding claims, wherein the solid perfume composition comprises the lipid component in an amount of from 25 wt.% to 95 wt.%, based on the total weight of the solid perfume composition, preferably from 25 wt.% to 70 wt.%.
10. The solid perfume composition according to any of the preceding claims, wherein the additional benefit agent includes absorbing agents, antioxidants, vitamins, dyes, and sweeteners.
11 . The solid perfume composition according to any of the preceding claims, wherein the solid perfume composition does not comprise an aqueous and/or an alcoholic liquid, preferably the solid perfume composition does not comprise water and/or ethanol.
12. A consumer product comprising the solid perfume composition according to any of the preceding claims.
13. The consumer product according to claim 12, wherein the consumer product is a personal care or cosmetic product.
14. The consumer product according to claim 13, wherein the consumer product is a solid and/or waterless personal care or cosmetic product, such as a solid perfumed stick or a waterless perfumed balm.
15. Use of a solid perfume composition according to any of claims 1 to 11 for enhancing and/or prolonging the perfume performance.
PCT/EP2025/069104 2024-07-09 2025-07-04 Solid perfume compositions Pending WO2026012919A1 (en)

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