WO2018050655A1 - Perfuming composition - Google Patents

Perfuming composition Download PDF

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Publication number
WO2018050655A1
WO2018050655A1 PCT/EP2017/072929 EP2017072929W WO2018050655A1 WO 2018050655 A1 WO2018050655 A1 WO 2018050655A1 EP 2017072929 W EP2017072929 W EP 2017072929W WO 2018050655 A1 WO2018050655 A1 WO 2018050655A1
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methyl
composition
perfuming
yl
characterized
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PCT/EP2017/072929
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French (fr)
Inventor
François-Raphael BALESTRA
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Firmenich Sa
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q13/00Formulations or additives for perfume preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/342Alcohols having more than seven atoms in an unbroken chain
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET 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
    • A61K2800/59Mixtures
    • A61K2800/591Mixtures of compounds not provided for by any of the codes A61K2800/592 - A61K2800/596

Abstract

The present invention concerns a composition comprising a) 4-methyl-2-pentylpyridine; and b) at least one ingredient, in the form of any one of its stereoisomers, selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2- buten-l-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol, 1-methyl- 2-[(l',2',2'-trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl]methynol, 2-methyl-4- (2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-l-ol, a- or /?-santalol and mixture thereof; characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.5% to 5% w/w, percentage being relative to the total weight of ingredients of lists a) and b); and the use as a perfumery ingredient of said composition.

Description

PERFUMING COMPOSITION

Technical field

The present invention relates to the field of perfumery. More particularly, it concerns a perfuming composition comprising

a) 4-methyl-2-pentylpyridine; and

b) at least one ingredient, in the form of any one of its stereoisomers, selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2- buten-l-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol, [1-methyl- 2-[(l',2',2'-trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl]methynol, 2-methyl-4- (2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-l-ol, a- or ?-santalol and mixture thereof; characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.5% to 5% w/w, percentage being relative to the total weight of ingredients of lists a) and b).

Following what is mentioned herein, the invention's perfuming composition as a part of a perfuming consumer product and the use of the invention's perfuming composition are also objects of the invention.

Prior art

Sandalwood oil is a very appreciated perfuming ingredient imparting a warm woody connotation having a typical creamy note. However, as all natural perfuming ingredients, the amount of the sandalwood oil available on market, the quality and the price of said oil are very fluctuating motivating the perfuming industry to develop replacer such as 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2-buten-l-ol, 3,3- dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol or 2-methyl-4-(2,2,3- trimethyl-3-cyclopenten-l-yl)-4-penten-l-ol. Nonetheless, the industry is still interested in new solution to improve the imparting of the creamy-milky connotation of sandalwood oil.

The present invention provides a solution to the above mentioned problem by using composition comprising 4-methyl-2-pentylpyridine and at least one ingredient selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2- buten-l-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol, [1- methyl-2-[(r,2',2'-trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl]methynol, 2- methyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-l-ol, - or ?-santalol and mixture thereof; wherein 4-methyl-2-pentylpyridine is present in an specific amount. 4- methyl-2-pentylpyridine has been reported in WO 2011/121469 to impart a green, green bean note, as well as a spicy-bell pepper, paprika note, and a green, pyrazinic bottom note. In view of its organoleptic profile, it is very surprising that it may boost confer, enhance or improve the missing creamy-milky note of the synthetic replacer of sandalwood oil. Said composition has not been disclosed or suggested heretofore.

Description of the invention

Surprisingly, it has now been discovered that the addition of 4-methyl-2- pentylpyridine to a perfuming composition possessing a woody ogarnoleptic character and in particular sandalwood character allows enhancing the creamy-milky-sandalwood note.

Therefore the first object of the present invention is a perfuming composition comprising

a) 4-methyl-2-pentylpyridine; and

b) at least one ingredient, in the form of any one of its stereoisomers, selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2-buten-l-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol, [l-methyl-2-[(l',2',2'- trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl]methynol, 2-methyl-4-(2,2,3- trimethyl-3-cyclopenten-l-yl)-4-penten-l-ol, a- or ?-santalol and mixture thereof;

characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.5% to 5% w/w, percentage being relative to the total weight of ingredients of lists a) and b);

said composition can be used to impart or boost the odor notes of the sandalwood type including the milky/creamy aspect typical of the sandalwood oil.

According to any one of the invention embodiments, the invention's perfuming composition may comprise

a) 4-methyl-2-pentylpyridine; and

b) at least one ingredient, in the form of any one of its stereoisomers, selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2-buten-l-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol, 2-methyl-4-(2,2,3- trimethyl-3-cyclopenten-l-yl)-4-penten-l-ol and mixture thereof; characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.5% to 5% w/w, percentage being relative to the total weight of ingredients of lists a) and b).

According to any one of the invention embodiments, the invention's perfuming composition may comprise 4-methyl-2-pentylpyridine in an amount comprised between 1% to 4% w/w, preferably between 1.5% and 3 % w/w, percentage being relative to the total weight of ingredients of lists a) and b).

According to any one of the invention embodiments, 2-ethyl-4-(2,2,3-trimethyl-3- cyclopenten-l-yl)-2-buten-l-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4- penten-2-ol, [l-methyl-2-[(r,2',2'-trimethylbicyclo[3.1.0]hex-3'- yl)methyl]cyclopropyl]methynol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4- penten-l-ol, a- or ?-santalol may be in a form of any stereoisomers; e.g. (l'R,E)-2-ethyl- 4-(2',2',3'-trimethyl-3'-cyclopenten-r-yl)-2-buten-l-ol, (l'S,3¾)-[l-methyl-2-[(l',2',2'- trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl]methynol or (-)-(l'S,2'R,Z)-2- methyl-5-(2'-methyl-3'-methylene-bicyclo[2.2.1]hept-2'-yl)-2-penten-l-ol. Some ingredients of group b) like santalol may be present in natural oils; e.g. sandalwood oil which is also part of the present invention. In such a case, the addition of 4-methyl-2- pentylpyridine to a composition comprising sandalwood oil boosts the milky note present in sandalwood oil.

For the sake of clarity, by the expression "any stereoisomers", or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the compounds can be a pure enantiomer (if chiral) or diastereomer (e.g. the double bond is in a conformation E or Z) or a mixture of enantiomer or diastereoisimer.

The addition of 4-methyl-2-pentylpyridine to a perfuming composition comprising perfuming ingredients imparting woody note and more specifically sandalwood note despite the organoleptic property of said ingredient which is known to provide a spicy and green note, allows boosting the creamy-milky aspect lacking of the perfuming composition leading to a more natural note.

According to a particular embodiment, the invention's perfuming composition may be used as a perfume on its own. So, the invention's perfuming composition may consist of 4-methyl-2-pentylpyridine; and at least one ingredient selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2-buten-l-ol, 3,3-dimethyl-5- (2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol, [l-methyl-2-[(l',2',2'- trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl]methynol, 2-methyl-4-(2,2,3- trimethyl-3-cyclopenten-l-yl)-4-penten-l-ol, a- or ?-santalol and mixture thereof characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.5% to 5% w/w, percentage being relative to the total weight of ingredients of lists a) and b).

A perfuming composition is a complex mixture including a multitude of ingredients imparting different olfactive notes. A perfuming composition is shaped in order to provide an odor presenting different organoleptic facets. So, according to another particular embodiment, the invention's perfuming composition may be part of a more complex perfuming composition wherein the invention composition is added in order to improve the hedonic aspect of a composition, in particular the sandalwood type aspect. So the perfuming composition of the present invention may further comprise optional ingredient such as perfumery carrier, perfuming co-ingredient or perfumery adjuvant. With the addition of optional ingredients, the ingredients of list a) and b) may be present in the composition in an amount comprised between 1% and 99% w/w, percentage being relative to the total weight of the composition, preferably between 1% to 10% and 4- methyl-2-pentylpyridine may be present in an amount comprised between 0.01 % to 5% w/w, percentage being relative to the total weight of the composition; preferably in an amount comprised between 0.02 % to 0.4% w/w, more preferably in an amount comprised between 0.02 % to 0.1% w/w.

According to a particular embodiment, the invention's perfuming composition may optionally comprise a perfumery carrier. By "perfumery carrier" it is meant a material which is practically neutral from a perfumery point of view, i.e. that does not significantly alter the organoleptic properties of perfuming ingredients. Said carrier may be a liquid or a solid.

As liquid carrier one may cite, as non-limiting examples, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive. However, one can cite as non-limiting examples solvents such as butylene or propylene glycol, glycerol, dipropyleneglycol and its monoether, 1,2,3- propanetriyl triacetate, dimethyl glutarate, dimethyl adipate l,3-diacetyloxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2- (2- ethoxyethoxy)-l-ethano, tri-ethyl citrate or mixtures thereof, which are the most commonly used. Other suitable perfumery carriers than those previously specified, can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol (origin: Dow Chemical Company), or hydrogenated castors oils such as those known under the trademark Cremophor RH 40 (origin: BASF).

Solid carrier is meant to designate a material to which the perfuming composition or some element of the perfuming composition can be chemically or physically bound. In general such solid carriers are employed either to stabilize the composition, or to control the rate of evaporation of the compositions or of some ingredients. The use of solid carrier is of current use in the art and a person skilled in the art knows how to reach the desired effect. However by way of non-limiting example of solid carriers, one may cite absorbing gums or polymers or inorganic materials such as porous polymers, cyclodextrines, wood based materials, organic or inorganic gels, clays, gypsum talc or zeolites.

As other non-limiting example of solid carriers, one may cite encapsulating materials. Examples of such materials may comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloide: Stabilisatoren, Dickungs- und Geliermittel in Lebensmitteln, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualitat, Behr's Verlag GmbH & Co., Hamburg, 1996. The encapsulation is a well-known process to a person skilled in the art, and may be performed, for instance, by using techniques such as spray-drying, agglomeration or yet extrusion; or consists of a coating encapsulation, including coacervation and complex coacervation technique.

As other non-limiting examples of solid carriers, one may cite the core-shell capsules with resins of aminoplast, polyamide, polyester, polyurea or polyurethane type or a mixture thereof (all of said resins are well known to a person skilled in the art) using techniques like phase separation process induced by polymerization, interfacial polymerization, coacervation or altogether (all of said techniques have been described in the prior art), optionally in the presence of a polymeric stabilizer or of a cationic copolymer.

Resins may be produced by the polycondensation of an aldehyde (e.g. formaldehyde, 2,2-dimethoxyethanal, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with an amine such as urea, benzoguanamine, glycoluryl, melamine, methylol melamine, methylated methylol melamine, guanazole and the like, as well as mixtures thereof. Alternatively one may use preformed resins alkylolated polyamines such as those commercially available under the trademark Urac® (origin: Cytec Technology Corp.), Cy mel® (origin: Cytec Technology Corp.), Urecoll® or Luracoll® (origin: BASF).

Others resins are the ones produced by the polycondensation of an a polyol, like glycerol, and a polyisocyanate, like a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or a Biuret of hexamethylene diisocyanate or a trimer of xylylene diisocyanate with trimethylolpropane (known with the tradename of Takenate®, origin: Mitsui Chemicals), among which a trimer of xylylene diisocyanate with trimethylolpropane and a Biuret of hexamethylene diisocyanate.

Some of the seminal literature related to the encapsulation of perfumes by polycondensation of amino resins, namely melamine based resins with aldehydes includes articles such as those published by K. Dietrich et al. in Acta Polymerica, 1989, vol. 40, pages 243, 325 and 683, as well as 1990, vol. 41, page 91. Such articles already describe the various parameters affecting the preparation of such core-shell microcapsules following prior art methods that are also further detailed and exemplified in the patent literature. US 4'396'670, to the Wiggins Teape Group Limited is a pertinent early example of the latter. Since then, many other authors have enriched the literature in this field and it would be impossible to cover all published developments here, but the general knowledge in encapsulation technology is very significant. More recent publications of pertinency, which disclose suitable uses of such microcapsules, are represented for example by the article of H.Y.Lee et al. in Journal of Microencapsulation, 2002, vol. 19, pages 559-569, international patent publication WO 01/41915 or yet the article of S. Bone et al. in Chimia, 2011, vol. 65, pages 177-181.

According to a particular embodiment, the invention's perfuming composition may optionally comprise further perfuming co-ingredients. Said perfuming co-ingredients is not selected from the list consisting of 4-methyl-2-pentylpyridine, 2-ethyl-4-(2,2,3- trimethyl-3-cyclopenten- l-yl)-2-buten- l-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3- cyclopenten-l-yl)-4-penten-2-ol, [l-methyl-2-[( ,2',2'-trimethylbicyclo[3.1.0]hex-3'- yl)methyl]cyclopropyl]methynol, 2-methyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4- penten-l-ol, a- or ?-santalol. Moreover, by "perfuming co-ingredient" it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect. In other words such a co-ingredient, to be considered as being a perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.

The nature and type of the perfuming co-ingredients optionally present in the perfuming composition 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 his general knowledge and according to the intended use or application and the desired organoleptic effect. In general terms, these perfuming co -ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.

In particular one may cite perfuming co-ingredients which are commonly used in perfume formulations, such as:

- Aldehydic ingredients: decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal and/or nonenal;

- Aromatic-herbal ingredients: eucalyptus oil, camphor, eucalyptol, menthol and/or alpha-pinene;

- Balsamic ingredients: coumarine, ethylvanillin and/or vanillin;

- Citrus ingredients: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, l-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- l-yl)-3-buten- 2-one, hexyl salicylate, 3,7-dimethyl-l,6-nonadien-3-ol, 3-(4-isopropylphenyl)-2- methylpropanal, verdyl acetate, geraniol, P-menth-l-en-8-ol, 4-(l,l-dimethylethyl)-l- cyclohexyle acetate, l,l-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2- butanol, amyl salicylate , high cis methyl dihydrojasmonate, 3-methyl-5-phenyl-l- pentanol, verdyl proprionate, geranyl acetate, tetrahydro linalool, cis-7-P-menthanol, Propyl (S)-2-(l,l-dimethylpropoxy)propanoate, 2-methoxynaphthalene, 2,2,2- trichloro- 1-phenylethyl acetate, 4/3-(4-hydroxy-4-methylpentyl)-3-cyclohexene- 1- carbaldehyde, amylcinnamic aldehyde, 4-phenyl-2-butanone, isononyle acetate, 4-(l,l- dimethylethyl)-l-cyclohexyl acetate, verdyl isobutyrate and/or mixture of methylionones isomers;

- Fruity ingredients: gamma undecalactone, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma nonalactone, allyl heptanoate, 2- phenoxyethyl isobutyrate, ethyl 2-methyl-l,3-dioxolane-2-acetate and/or diethyl 1,4- cyclohexane dicarboxylate;

- Green ingredients: 2,4-Dimethyl-3-cyclohexene-l -carbaldehyde, 2-tert-butyl-l- cyclohexyl acetate, styrallyl acetate, allyl (2-methylbutoxy)acetate, 4-methyl-3-decen- 5-ol, diphenyl ether, (Z)-3-hexen-l-ol and/or l-(5,5-dimethyl-l-cyclohexen-l-yl)-4- penten-l-one;

- Musk ingredients: l,4-dioxa-5,17-cycloheptadecanedione, pentadecenolide, 3-Methyl- 5-cyclopentadecen-l-one, 1, 3,4,6,7, 8-hexahydro-4,6, 6,7,8, 8-hexamethyl-cyclopenta-g- 2-benzopyrane, (lS, R)-2-[l-(3',3'-dimethyl-l'-cyclohexyl)ethoxy]-2-methylpropyl propanoate, pentadecanolide and/or (lS, R)-[l-(3',3'-Dimethyl-l'- cyclohexyl)ethoxycarbonyl]methyl propanoate;

- Woody ingredients: l-(octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-l-ethanone, patchouli oil, terpenes fractions of patchouli oil, Methyl cedryl ketone, 5-(2,2,3- trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, l-(2,3,8,8-tetramethyl- 1,2,3,4,6,7, 8, 8a-octahydronaphthalen-2-yl)ethan-l -one and/or isobornyl acetate;

- Other ingredients (e.g. amber, powdery spicy or watery): dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,l-b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, clove oil, 3-(l,3-benzodioxol-5-yl)-2- methylpropanal and/or 3-(3-isopropyl-l-phenyl)butanal.

A perfumery co-ingredients according to the invention may not be limited to the above mentioned perfuming co-ingredients, and many other 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. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.

According to a particular embodiment, the invention's perfuming composition may optionally comprise perfumery adjuvant. By "perfumery adjuvant" we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming composition cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art. One may cite as specific non-limiting examples the following: viscosity agents (e.g. surfactants, thickeners, gelling and/or rheology modifiers), stabilizing agents (e.g. preservatives, antioxidant, heat/light and or buffers or chelating agents, such as BHT), coloring agents (e.g. dyes and/or pigments), preservatives (e.g. antibacterial or antimicrobial or antifungi or anti irritant agents), abrasives, skin cooling agents, fixatives, insect repellants, ointments, vitamins and mixtures thereof.

It is understood that a person skilled in the art is perfectly able to design optimal formulations for the desired effect by admixing the above mentioned components of a perfuming composition, simply by applying the standard knowledge of the art as well as by trial and error methodologies.

An invention's composition consisting of at least one invention's composition as defined above and at least one perfumery carrier consists of a particular embodiment of the invention as well as a perfuming composition comprising at least invention's composition as defined above, at least one perfumery carrier, at least one perfumering co- ingredient, and optionally at least one perfumery adjuvant.

For the sake of clarity, it is also understood that any mixture resulting directly from a chemical synthesis, e.g. a reaction medium without an adequate purification, in which the composition of the invention would be involved as a starting, intermediate or end-product could not be considered as a perfuming composition according to the invention as far as said mixture does not provide the inventive composition in a suitable form for perfumery. Thus, unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.

The invention's composition can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to positively impart or modify the odor of a consumer product into which said composition is added. Consequently, another object of the present invention consists of a perfumed consumer product comprising, as a perfuming ingredient, the invention's composition, as defined above.

The invention's composition can be added as such or as part of an invention's perfuming composition.

For the sake of clarity, "perfumed consumer product" is meant to designate a consumer product which deliver at least a pleasant perfuming effect to the surface or space to which it is applied (e.g. skin, hair, textile, or home surface). In other words, a perfumed consumer product according to the invention is a perfumed consumer product which comprises a functional formulation, as well as optionally additional benefit agents, corresponding to the desired consumer product, and an olfactive effective amount of at least one invention's compound. For the sake of clarity, said perfumed consumer product is a non-edible product.

The nature and type of the constituents of the perfumed consumer product 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 his general knowledge and according to the nature and the desired effect of said product.

Non-limiting examples of suitable perfumed consumer product include a perfume, such as a fine perfume, a splash or eau de parfum, a cologne or a shave or after- shave lotion; a fabric care product, such as a liquid or solid detergent, a fabric softener, a liquid or a solid scent booster, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product; a body-care product, such as a hair care product (e.g. a shampoo, a coloring preparation or a hair spray, a color care product, a hair shaping product, a dental care product), a disinfectant, an intimate care product; a cosmetic preparation (e.g. a skin cream or lotion, a vanishing cream or a deodorant or antiperspirant (e.g. a spray or roll on), a hair remover, a tanning or sun or after sun product, a nail product, a skin cleansing, a makeup); or a skin-care product (e.g. a soap, shower or bath mousse, an oil or a gel, or a hygiene product or a foot/hand care products); an air care product, such as an air freshener or a "ready to use" powdered air freshener which can be used in the home space (rooms, refrigerators, cupboards, shoes or car) and/or in a public space (halls, hotels, malls, etc.); or a home care product, such as a mold remover, a furnisher care, a wipe, a dish detergent or a hard-surface (e.g. a floor, bath, sanitary or a windows) detergent; a leather care product; a car care product, such as a polish, a waxe or a plastic cleaners. Some of the above-mentioned perfumed consumer product may represent an aggressive medium for the invention's composition, so that it may be necessary to protect the latter from premature decomposition, for example by encapsulation or by chemically binding it to another chemical which is suitable to release the invention's composition upon a suitable external stimulus, such as an enzyme, light, heat or a change of pH.

The proportions in which the composition according to the invention can be incorporated into the various aforementioned products or compositions vary within a wide range of values. These values are dependent on the nature of the article to be perfumed and on the desired organoleptic effect as well as on the nature of the co-ingredients in a given base when the invention's composition according to the invention are mixed with perfuming co-ingredients, solvents or additives commonly used in the art.

When the invention composition are incorporated into perfumed consumer products, other than fine perfumery and air freshener where in general the perfuming composition is the essential constituent of a consumer product, 0.01% to 2% by weight of the invention's composition can be used, percentage being relative to the weight of the article.

Another object of the present invention is the use of a composition as defined above as perfuming ingredient. In other words, it concerns a method or a process to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article or of a surface, which method comprises adding to said composition or article an effective amount of invention's composition as defined above, e.g. to impart its typical note.

According to a particular embodiment, such method is aimed to provide a more natural sandalwood note of a perfuming composition or of a consumer product.

Examples

Example 1 Preparation of a perfuming composition

A perfuming composition, of the woody type, was prepared by admixing the following ingredients: Parts by weight Ingredient

Cedar oil 400

Dartanol®1} 200

Dipropylene Glycol 200

Iso E Super®2) 4000

Vetyver oil .200

5000

1) (rR,E)-2-ethyl-4-(2',2',3'-trimethyl-3'-cyclopenten- r-yl)-2-buten-l-ol; origin:

Firmenich SA, Geneva, Switzerland

2) l-(octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)- 1 -ethanone; origin:

International Flavors & Fragrances, USA

The addition of 4 parts of by weight of 4-methyl-2-pentylpyridine (i.e. 2% w/w of 4-methyl-2-pentylpyridine, percentage being relative to the total weight of ingredients of lists a) and b)) to the above-described composition imparted to the latter a creamy and milky connotation providing to said composition a sandalwood odor closer to the sandalwood oil. Without addition of 4-methyl-2-pentylpyridine, said composition lacks creamy note typical of natural sandalwood oil.

Then, the perfuming composition of the woody type was diluted in dipropylene glycol up to 10000 parts by weight; i.e 4996 parts of dipropylene glycol was added to the above- described composition comprising 4 parts by weight of 4-methyl-2-pentylpyridine.

Example 2

Preparation of a eau de toilette comprising the invention's composition

The eau de toilette was prepared by adding 5 to 15% by weight, relative to the total weight of the eau de toilette, of said perfuming composition into ethanol under gentle shaking. Example 3

Preparation of a structured shower gel comprising the invention's composition Table 1: Composition of the structured shower gel formulation

Figure imgf000014_0001

1) EDETA B POWDER; trademark and origin: BASF

2) ZETESOL AO 328 U; trademark and origin: ZSCHIMMER & SCHWARZ

3) TEGO-BETAIN F 50; trademark and origin: GOLDSCHMIDT

4) MERQUAT 550; trademark and origin: LUBRIZOL

The structured shower gel was prepared by adding 0.5 to 1% by weight, relative to the total weight of the shower gel, of the invention's composition of example 1 into the unperfumed shower gel formulation of Table 1 under gentle shaking. Example 4

Preparation of a transparent shower gel comprising the invention's composition

Table 2: Composition of the transparent shower gel formulation

Ingredients Concentration (%

wt)

WATER deionized 52.40 Tetrasodium EDTA 1} 0.10

Sodium Benzoate 0.50

Propylene Glycol 2.00

Sodium C12-C15 Pareth Sulfate 2) 35.00

Cocamidopropyl Betaine ) 8.00

Polyquaternium-74) 0.20

Citric Acid (40%) 1.00

Sodium Chloride 0.80

1) EDETA B POWDER; trademark and origin: BASF

2) ZETESOL AO 328 U; trademark and origin: ZSCHIMMER & SCHWARZ

3) TEGO-BETAIN F 50; trademark and origin: GOLDSCHMIDT

4) MERQUAT 550; trademark and origin: LUBRIZOL The transparent shower gel was prepared by adding 0.5 to 1% by weight, relative to the total weight of the shower gel, of the invention's composition of example 1 into the unperfumed shower gel formulation of Table 2 under gentle shaking.

Example 5

Preparation of a milky shower gel comprising the invention's composition

Table 3: Composition of the milky shower gel formulation

Figure imgf000015_0001
Glycol Distearate & Laureth-4 & Cocamidopropyl Betaine6) 3.000

Sodium Chloride 20% 5.000

PEG-40 Hydrogenated Castor Oil7) 1.000

1) EDETA B POWDER; trademark and origin: BASF

2) Texapon NSO IS; trademark and origin: COGNIS

3) MERQUAT 550; trademark and origin: LUBRIZOL

4) DEHYTON AB-30; trademark and origin: COGNIS

5) GLUCAMATE LT; trademark and origin: LUBRIZOL

6) EUPERLAN PK 3000 AM; trademark and origin: COGNIS

7) CREMOPHOR RH 40; trademark and origin: BASF

The transparent shower gel was prepared by adding 0.5 to 1% by weight, relative to the total weight of the shower gel, of the invention's composition of example 1 into the unperfumed shower gel formulation of Table 3 under gentle shaking.

Claims

Claims
1. A perfuming composition comprising
a) 4-methyl-2-pentylpyridine; and
b) at least one ingredient, in the form of any one of its stereoisomers, selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2- buten-l-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol, [1-methyl- 2-[(l',2',2'-trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl]methynol, 2-methyl-4- (2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-l-ol, a- or ?-santalol and mixture thereof; characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.5% to 5% w/w, percentage being relative to the total weight of ingredients of lists a) and b).
2. The perfuming composition according to claim 1; characterized in that the perfuming composition comprises 4-methyl-2-pentylpyridine in an amount comprised between 1% to 4% w/w, percentage being relative to the total weight of ingredients of lists a) and b).
3. The perfuming composition according to claim 2; characterized in that the perfuming composition comprises 4-methyl-2-pentylpyridine in an amount comprised between 1.5% and 3 % w/w, percentage being relative to the total weight of ingredients of lists a) and b).
4. The perfuming composition according to any one of claims 1 to 3; characterized in that the perfuming composition further comprises a perfumery carrier.
5. The perfuming composition according to any one of claims 1 to 4; characterized in that the perfuming composition further comprises at least one perfuming co-ingredient.
6. The perfuming composition according to any one of claims 1 to 5; characterized in that the perfuming composition further comprises a perfumery adjuvant.
7. The perfuming composition according to any one of claims 1 to 6, characterized in that the ingredients of list a) and b) are present in the composition in an amount comprised between 1% and 99% w/w, percentage being relative to the total weight of the composition.
8. The perfuming composition according to any one of claims 1 to 7, characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.01 % to 5% w/w, percentage being relative to the total weight of the composition.
9. The perfuming composition according to any one of claims 1 to 3, characterized in that the perfuming composition consists of
a) 4-methyl-2-pentylpyridine; and
b) at least one ingredient, in the form of any one of its stereoisomers, selected from the group consisting of 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten-l-yl)-2- buten-l-ol, 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-2-ol, [1-methyl- 2-[(l',2',2'-trimethylbicyclo[3.1.0]hex-3'-yl)methyl]cyclopropyl]methynol, 2-methyl-4- (2,2,3-trimethyl-3-cyclopenten-l-yl)-4-penten-l-ol, a- or ?-santalol and mixture thereof; characterized in that 4-methyl-2-pentylpyridine is present in an amount comprised between 0.5% to 5% w/w, percentage being relative to the total weight of ingredients of lists a) and b).
10. Use as perfuming ingredient of a composition as defined in claims 1 to 9.
11. A method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of a composition as defined in claims 1 to 9.
12. A perfuming consumer product comprising a composition, as defined in any one of claims 1 to 9.
13. The perfumed consumer product according to claim 12, characterized in that the perfumery consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product.
14. The perfumed consumer product according to claim 13, characterized in that the perfumery consumer product is a fine perfume, a splash or eau de parfum, a cologne, a shave or after-shave lotion, a liquid or solid detergent, a fabric softener, a liquid or solid scent booster, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, shower or bath mousse, oil or gel, or a foot/hand care products, a hygiene product, an air freshener, a "ready to use" powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or hard-surface detergent, a leather care product or a car care product.
PCT/EP2017/072929 2016-09-16 2017-09-12 Perfuming composition WO2018050655A1 (en)

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