EP3601509A1 - Mélanges de parfums contenant du tricyclo[5.2.1.0]-décan-8-éthyléther - Google Patents

Mélanges de parfums contenant du tricyclo[5.2.1.0]-décan-8-éthyléther

Info

Publication number
EP3601509A1
EP3601509A1 EP17713214.9A EP17713214A EP3601509A1 EP 3601509 A1 EP3601509 A1 EP 3601509A1 EP 17713214 A EP17713214 A EP 17713214A EP 3601509 A1 EP3601509 A1 EP 3601509A1
Authority
EP
European Patent Office
Prior art keywords
formula
compound
fragrances
perfume
fragrance
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
EP17713214.9A
Other languages
German (de)
English (en)
Inventor
Bernd HÖLSCHER
Marc MANSFELD
Tobias Wagner
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.)
Symrise AG
Original Assignee
Symrise AG
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 Symrise AG filed Critical Symrise AG
Publication of EP3601509A1 publication Critical patent/EP3601509A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Definitions

  • the present invention relates primarily to certain perfume mixtures, preferably perfume oils, comprising a compound of the formula (I) (tricyclo [5.2.1.0] decane-8-ethyl ether)
  • the present invention relates to processes for the preparation of perfume mixtures according to the invention, in particular perfume oils, perfumed products containing a fragrance mixture according to the invention, processes for the preparation of perfumed products according to the invention and the use of the compound of formula (I) for enhancing the natural freshness and / or radiance and / or for masking or reducing greasy, technical and / or metallic notes of one or more fragrances other than the compound of formula (I).
  • the compound of the formula (I) is known to the person skilled in the art (CAS No. 13213-08-6, see also Zhurnal Obshchei Khimii (1964), 34 (6), 2081-4).
  • An odor description of the compound of the formula (I) can be found in DE 3501888 C2.
  • the compound of formula (I) is described there as strong, warm woody, strongly radiant and with a note pronounced of forest foliage.
  • perfumery the compound of formula (I) has so far found no appreciable application.
  • a fragrance mixture according to the invention (as described herein) or even preferred or advantageous amounts (ratios) is not known in the prior art.
  • certain odor effects when combined with fragrances of components (b) or (c) have not previously been described.
  • the compound of formula (I) can be used e.g. by alkylation of tricyclo [5.2.1.0] decan-8-ol by addition of ethanol to dicyclopentadiene and subsequent hydrogenation.
  • ethanol can alternatively be added to dicyclopentadiene using acidic ion exchangers (analogously to DE 2642519 A1) and then hydrogenated under a hydrogen atmosphere:
  • the product thus prepared has, in particular, the following odor properties: floral, green, fruity orange.
  • the compound of formula (I) may be in any stereoisomeric form or may be present as any mixture of stereoisomers (e.g., exo / endo isomer mixture, mixture of diastereomers, racemate). According to a preferred embodiment of the present invention (as described herein), it is present as a mixture of two or more stereoisomers (see, for example, example 7, isomers I-IV (preferred combination of stereoisomers to be used according to the invention)).
  • Floral fragrances play an important role in perfumery. There is a constant need to emphasize (emphasize) certain odor aspects of a fragrance or perfume mixture. In the case of floral fragrances, this applies in particular to their natural freshness and charisma. Likewise, there is a continuing need to mask or lessen certain odor aspects of a fragrance or fragrance mixture. In the case of floral fragrances this applies in particular to greasy, technical and metallic notes.
  • the primary object of the present invention was to provide new, beneficial fragrance mixtures. It was also an object to emphasize or highlight certain odoriferous aspects of certain fragrances or perfume mixtures and / or to mask or reduce certain odoriferous aspects of a fragrance or fragrance mixture, in particular greasy and metallic notes.
  • the primary object is achieved by a fragrance mixture, preferably by a perfume oil, comprising the constituents Compound of the formula (I)
  • Odor note from the group consisting of alcohols and aldehydes with a molecular weight of 210 g / mol or less,
  • fragrances fragrance (s) from the group consisting of ketones, ethers and esters having a molecular weight in the range of 190 g / mol to 250 g / mol.
  • Fragrance mixtures according to the invention are preferably liquid at 25 ° C. and 1013 hPa and are usually homogeneous solutions.
  • the compound of formula (I) causes certain odor aspects of the perfume (s) of ingredient (b) and / or perfume (s) of ingredient (c) to be emphasized and / or masked or reduced become.
  • greasy, technical and metallic notes of the fragrances of components (b) and / or (c) are effectively masked or reduced by the compound of formula (I).
  • a fragrance mixture according to the invention preferably a perfume oil
  • the person skilled in the art can choose the proportion of component (a), ie the proportion of the compound of formula (I), such that the effect of the concrete (highlighting) and / or masking desired thereby or, if necessary, reducing an odor note, and if necessary taking care not to use too much of the constituent (a) which might dominate the overall sensory impression of a perfume mixture and not merely providing such a small amount of the constituent (a) that an emphasis or masking / reduction of odoriferous aspects of fragrances of component (b) or (c) is not or hardly noticeable.
  • the proportion of component (a) ie the proportion of the compound of formula (I)
  • the compound of formula (I) in addition to their primary sensory properties additional positive secondary properties, such as high stability under certain conditions of use (in alkaline media (washing powder, laundry, soap, shampoo, etc.), a high degree of flexibility , has good adhesion and high substantivity, and this property is quite surprising for an ether having a molecular weight of 180 g / mol.
  • Component (b) of the fragrance mixture according to the invention consists of or comprises one or more fragrances from the group consisting of alcohols and aldehydes having a molecular weight of 210 g / mol or less.
  • these fragrances Preferably, these fragrances have a floral odor note.
  • Such fragrances are known to the person skilled in the art.
  • fragrance mixtures according to the invention preferably perfume oils, where component (b) comprises or consists of two, three, four, five or more different fragrances.
  • the mass ratio of the total amount of perfume (s) of the component (b) to the compound of formula (I) is greater than or equal to 99: 1, preferably greater than or equal to 99.9: 0, 1, more preferably greater or equal to 99.999: 0.001.
  • these mass ratios are particularly advantageous.
  • the intrinsic odor of the compound of the formula (I) is no longer or hardly perceptible on a regular basis, but the presence of the compound of the formula (I) has a positive influence on the overall grade of the fragrance mixture according to the invention. It is particularly surprising that the compound of the formula (I) has an effect on the freshness and charisma of the perfume mixture even at low concentrations, without causing or emphasizing to a relevant extent a fruity odor.
  • perfume mixtures according to the invention preferably to perfume oils according to the invention, where the one, several or all fragrances of component (b) is or are selected from the group consisting of 2-methyl-3- (4-tert-butylphenyl) propanal, 4 - (4-hydroxy-4-methylpentyl) -3-cyclohexenecarboxaldehyde, 2- Methyl 4- (2,2,6-trimethyl-1-cyclohexen-1-yl) -2-butenal, 1-methyl-4- (4-methyl-3-penten-1-yl) -3-cyclohexenecarboxaldehyde , 3- (3-Isopropyl-phenyl) -butyraldehyde, (E) -2,6,10-trimethyl-undeca-5,9-dienal, benzo [1,3] dioxole-5-carbaldehyde, 2,2-dimethyl 3-phenyl-propan-1-ol, 2,2-dimethyl-3-
  • fragrances according to the invention preferably perfume oils according to the invention, where the one, several or all fragrances of constituent (b) are or are selected from the group consisting of 1- (4-isopropylcyclohexyl) ethanol (mugetanol), E) -3,7-dimethyl-octa-2,6-dien-1-ol (geraniol), 3,7-dimethyl-oct-6-en-1-ol (citronellol), (4-isopropyl-cyclohexyl) methanol (mayol), 2-methyl-6-methylenoct-7-en-2-ol (myrcenol) (2-methyl-6-methylenoct-7-en-2-ol) and 2,6-dimethyl-octane 7-en-2-ol (dihydromyrcenol).
  • constituent (b) are or are selected from the group consisting of 1- (4-isopropylcyclohexyl) ethanol (mugetanol
  • fragrance mixtures according to the invention preferably perfume oils according to the invention, wherein the one, several or all fragrances of component (b) (each) have a molecular weight in the range from 140 to 170 g / mol.
  • component (b) is an alcohol or comprises an alcohol.
  • fragrances of component (b) are positively influenced by combination with a compound of formula (I).
  • a compound of formula (I) In individual cases, the sensory impression in the direction of natural, fresh, flowery, more aura, less technical, less greasy and / or less metallic shifted, which in individual cases, other sensory influences were observed. Further odor descriptions can be found in the attached examples.
  • fragrance mixtures according to the invention preferably perfume oils
  • component (c) comprises or consists of two, three, four, five or more different fragrances.
  • the fragrance (s) of the component (c) regularly act as the base note (s) of a fragrance mixture according to the invention or a perfume oil according to the invention.
  • the fragrances of component (c) are ketones, ethers and / or esters having a molecular weight in the range from 196 g / mol to 250 g / mol.
  • Fragrance mixtures according to the invention preferably perfume oils according to the invention, in which the mass ratio of the total amount of perfume (s) of component (c) to the total amount of compound of formula (I) is greater than or equal to 99: 1, preferably greater than or equal to 99.9, are particularly preferred Is: 0, 1, more preferably greater than or equal to 99.999: 0.001.
  • fragrances having a molecular weight in the range from 190 g / mol to 250 g / mol which may be part of component (c) are known to the person skilled in the art and can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vol and II, Montclair, NJ, 1969, Dverlag or H. Surburg, J. Panten, "Common Fragrance and Flavor Materials", 5 th Ed., Wiley-VCH, Weinheim 2006.
  • fragrance mixtures according to the invention preferably perfume oils according to the invention, wherein the fragrance or fragrances of component (c) are selected from the group consisting of methyl dihydrojasmonate, benzyl salicylate, cis-3-hexenyl salicylate, isoamyl salicylate, hexyl salicylate, 2,3,8,8-tetramethyl - 1,2,3,4,5,6,7,8-octahydro-2-naphthalenylmethylketone, linalyl acetate, ethyllyllactyl acetate, cedryl methyl ether, cedryl methyl ketone, cedryl acetate, (4aR, 5R, 7aS, 9R) octahydro-2,2,5 , 8,8,9a-hexamethyl-4H-4a, 9-methano-azuleno (5,6-d) -1,3-dioxole), 1 ', 1', 5', 5
  • Cyclododecylmethyl ether (ethoxymethoxy) cyclododecane, decahydro-naphthyl acetate, 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5 (-6) -indenyl acetate, allyl-3-cyclohexylpropionate, allylcyclohexyloxyacetate, benzyl benzoate , Benzyl cinnamate, oxacyclohexa-decane-2-one, 15-hydroxy-pentadecanonic acid lactone, 5-cyclohexadecen-1-one, 3-methyl-cyclopentadecenone, 1, 3,4,6J, 8-hexahydro-4,6,6J, 8 , 8-hexamethyl cyclopenta [g] -2-benzopyran, 2- [1- (3,3-dimethylcyclohexyl) ethoxy] -2-
  • fragrances of component (c) are positively influenced by combination with a compound of formula (I).
  • the compound of the formula (I) is preferably used at least in such an amount that a sensory effect is achieved (sensory effective amount).
  • a sensory effect is achieved by the presence of the compound of the formula (I) if a comparative fragrance mixture which contains no compound of the formula (I) with an otherwise identical composition is judged sensory differently than the fragrance mixture according to the invention.
  • the compound of the formula (I) is preferably used in a perfume mixture according to the invention in such a concentration that the sensory impression of the perfume mixture according to the invention is more natural, fresher, floral, more charismatic, less greasy, less technical and / or less Metallic is the sensory impression of a comparative fragrance mixture which, with an otherwise identical composition, contains no compound of the formula (I).
  • the mass ratio of the total amount of fragrances of components (b) and / or (c) to the total amount of compound of formula (I) is less than or equal to 99.999: 0.0001.
  • Fragrance mixtures according to the invention in particular perfume oils according to the invention, can be used in liquid form, undiluted or diluted with a solvent for perfuming or aromatization.
  • a solvent for perfuming or aromatization particularly suitable solvents for this purpose are ethanol, glycerol, 1,2-propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate and triacetin.
  • Alcohols and aldehydes having a molecular weight of 210 g / mol or less and ketones, ethers and esters having a molecular weight in the range of 190 g / mol to 250 g / mol are not included in components (b) and (c), respectively it is a compound selected from the group consisting of ethanol, isopropanol, glycerol, 1, 2-propylene glycol, 1, 2-butylene glycol, dipropylene glycol, diethyl phthalate and triacetin.
  • Fragrance mixtures according to the invention are preferably combined with further constituents, for example to produce products according to the invention described herein.
  • Preferred further constituents are selected from the group consisting of preservatives, preferably the abrasives, anti-acne agents and sebum reduction agents mentioned in US 2006/0089413, preferably the anti-aging agents mentioned in WO 2008/046791, preferably those in WO 2005 / 123101, antibacterial agents, anti-cellulite agents, anti-dandruff agents, preferably the anti-inflammatory agents mentioned in WO 2008/046795, anti-irritants, anti-irritants (anti-inflammatory, anti-irritant and anti-irritant agents), preferably those in WO 2007/042472 and US 2006 No.
  • the antioxidants mentioned in WO 2005/123101 preferably the astringents, antiseptics, antistats, binders, buffers, support materials mentioned in WO 2005/123101, preferably the chelating agents mentioned in WO 2005/123101 , preferably the cell stimulant mentioned in WO 2005/123101 cleaning agents, nourishing agents, depilatory agents, surfactants, deodorants and antiperspirants, preferably those described in WO 2005/123101, plasticizers, emulsifiers, preferably those mentioned in WO 2005/123101, enzymes, essential oils, preferably those mentioned in US 2008/0070825, insect repellents, preferably those mentioned in WO 2005/123101, fibers, film formers, fixatives, foaming agents , Foam stabilizers, foaming inhibitors, foam boosters, fungicides, gelling agents and gelling agents, preferably the hair care agents, hair styling agents, hair relaxers, moisture regulators mentioned in WO 2005/123101
  • moisture, moisturizing and / or moisturizing substances preferably the osmolytes mentioned in WO 2005/123101, preferably the compatible solutes mentioned in WO 2005/123101, preferably the bleaching agents mentioned in WO 01/76572 and WO 02/15686 toning agents, stain removing agents, optical brightening agents, impregnating agents, antisoiling agents, anti-friction agents, lubricants, moisturizers, ointments, opacifiers, plasticizers, topcoats, polishes, brighteners, polymers, preferably the powders mentioned in WO 2008/046676 , Proteins and protein hydrolysates, preferably the moisturizers, abrasives, skin soothing agents, skin cleansing agents, skin care agents, skin repair agents, preferably containing cholesterol and / or fatty acids and mentioned in WO 2005/123101 and WO 2008/046676 / or ceramides and / or pseudoceramides, preferably in WO 2006 Skin-
  • absorbing agents and UV filters preferably the benzylidene-beta-dicarbonyl compounds mentioned in WO 2005/123101, preferably the alpha-benzoylcinnamonitriles mentioned in WO 2005/107692, preferably the AhR receptor antagonists mentioned in WO 2006/015954, preferably the detergents, fabric softeners, suspending agents, skin tanning agents mentioned in WO 2007/128723 and WO 2007/060256, preferably the thickeners, vitamins, preferably mentioned in WO 2006/045760, preferably the oils, waxes and fats mentioned in WO 2005/123101 , preferably the phospholipids mentioned in WO 2005/123101, preferably the fatty acids mentioned in WO 2005/123101 (saturated fatty acids, or polyunsaturated fatty acids, ⁇ -hydroxy acids, polyhydroxy fatty acids), preferably the liquefiers, dyes and color protectants mentioned in WO 2005/123101, and also pigments, preferably the anti-corrosives, flavors
  • fragrances that are not already part of the ingredients (b) and (c) of a fragrance mixture according to the invention or a perfume invention, alcohols and polyols, preferably those in WO 2005/123101 surfactants, preferably those mentioned in WO 2005/123101, animal extracts, yeast extracts, extracts of algae or microalgae, electrolytes, plasticizers, organic solvents, preferably those mentioned in WO 2005/123101, or silicones and silicone derivatives, preferably those in WO 2008 / 046676.
  • compounds falling within the definition of components (b) and / or (c) are assigned to these components regardless of their intended use; for exceptions for certain solvents, see above.
  • perfume mixtures according to the invention in particular perfume oils according to the invention, can be adsorbed on a carrier which ensures both a fine distribution of the fragrances contained therein in the product and a controlled release during use.
  • Such carriers may be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc. or organic materials such as woods, cellulosic based substances, sugars, dextrins (e.g., maltodextrin), or plastics such as PVC, polyvinyl acetates or polyurethanes.
  • the combination of fragrance mixture according to the invention and carrier represents an exemplary product according to the invention (as described herein).
  • Fragrance mixtures according to the invention in particular perfume oils according to the invention, can also be microencapsulated, spray-dried, present as inclusion complexes or as extruded products (ie products according to the invention) and in this form e.g. be added to a perfumed product (also according to the invention).
  • compositions modified in this way can be further optimized by so-called “coating” with suitable materials with a view to a more targeted release of fragrance, using preferably wax-like plastics such as polyvinyl alcohol.
  • the microencapsulation of the perfume mixtures according to the invention can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, for example of polyurethane-type substances or soft gelatin.
  • the spray-dried fragrance mixtures can be prepared, for example, by spray-drying a fragrance mixture according to the invention, preferably a perfume oil, emulsion or dispersion, it being possible to use starches, proteins, dextrin and vegetable gums modified as carriers.
  • Inclusion complexes can be e.g. by introducing dispersions of the fragrance mixture according to the invention, preferably a perfume oil according to the invention, and cyclodextrins or urea derivatives into a suitable solvent, e.g. Water, to be produced.
  • a suitable solvent e.g. Water
  • Extrusion products may be prepared by fusing a fragrance mixture according to the invention, preferably a perfume oil according to the invention, with a suitable waxy substance and by extrusion with subsequent solidification, if appropriate in a suitable solvent, e.g. Isopropanol.
  • the invention also relates to a process for the preparation of a fragrance mixture, preferably a perfume oil, as described herein, comprising or consisting of the following step:
  • Preferred is a process wherein a fragrance mixture, preferably a perfume oil results, in the
  • the mass ratio of the total amount of perfume (s) of component (b) to the total amount of compound of formula (I) is greater than or equal to 99: 1, preferably greater than or equal to 99.9: 0, 1, particularly preferably greater than or equal to 99.999: Is 0.001,
  • the mass ratio of the total amount of perfume (s) of component (c) to the total amount of compound of formula (I) is greater than or equal to 99: 1, preferably greater than or equal to 99.9: 0, 1, particularly preferably greater than or equal to 99.999: Is 0.001.
  • the invention also relates to a method for enhancing the natural freshness and / or radiance and / or masking or reducing greasy, technical and / or metallic notes of one or more of the compound of formula (I) different fragrances, in particular one or more of the A compound of the formula (I) of various fragrances having a floral odor note, in particular jasmine, comprising the following step:
  • fragrance or fragrance (s) other than the compound of formula (I) with an amount of the compound of formula (I) sufficient to enhance the natural freshness and / or radiance of the fragrance or fragrances other than the compound of formula (I) and / or to mask or reduce greasy, technical and / or metallic notes.
  • the above statements on preferred fragrance mixtures according to the invention also apply correspondingly to such a method according to the invention.
  • the invention also relates to a perfumed product comprising a perfume mixture according to the invention, preferably an inventive perfume oil, wherein the perfume mixture is preferably contained in a sensory effective amount in the perfumed product.
  • "Sensory effective amount" in the present context means that the perfumed product according to the invention exhibits the sensory properties of the perfume mixture according to the invention during operation or during use.
  • Preferred perfumed products of the present invention are selected from the group consisting of perfume extracts, eau de perfumes, eau de toilettes, shaving waters, eau de colognes, pre-shave products, splash colognes, perfumed towelettes, acidic, alkaline and neutral detergents.
  • perfumed products according to the invention are selected from the following list:
  • Acid, alkaline and neutral detergents in particular in the household sector, preferably floor cleaner, window glass cleaner, dishwashing detergent, bath and sanitary cleaners, scouring cream, solid and liquid toilet cleaners, powder and foam carpet cleaners, liquid detergents, powder detergents, fabric softeners, surface disinfectants, in particular for hard surface cleaner;
  • Body care preparations preferably solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams;
  • oil-in-water, water-in-oil and water-in-oil-in-water type cosmetic emulsions preferably skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after -sun creams and lotions, Hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, skin tanning creams and lotions, skin lightening creams and lotions;
  • Hair care products preferably hair sprays, hair gels, firming hair lotions, hair conditioners, permanent and semipermanent hair dyes, hair lotions, hair creams and lotions;
  • Deodorants and antiperspirants preferably underarm sprays, roll-ons (preferably as alcoholic or non-alcoholic solution, as gel or (micro) emulsion, deodorant sticks, deodorants.
  • perfumed products according to the invention are detergents and cleaners, hygiene or care products, in particular in the field of body and hair care, cosmetics and household.
  • Preferred perfumed products according to the invention are those in which the proportion of the perfume mixture according to the invention or the proportion of total amount of constituents (a), (b) and / or (c) together on the perfumed product is 0.01 to 10% by weight 0, 1 to 5 wt .-% and particularly preferably 0.25 to 3 wt .-%, each based on the total mass of the perfumed product. This applies in particular to the preferred products mentioned above.
  • the invention also relates to a process for the preparation of a perfumed product consisting of or comprising the following steps:
  • step iii) contacting or mixing the further ingredient (s) provided in step ii) with a sensory effective amount of the perfume mixture provided or prepared in step i),
  • the amount of the compound of formula (I) is sufficient to preserve the natural freshness and / or radiance of one or more or to enhance all fragrances of ingredients (b) and / or (c) and / or to mask or reduce greasy, technical and / or metallic notes,
  • step (I) mixing the ingredient (s) provided in step (I) with the ingredients (b) and / or (c) of a perfume mixture according to the invention (as described herein) to give a mixture in which the ingredient or ingredients (b) and / or (c) are present in a sensory effective amount,
  • step III contacting or mixing the mixture prepared in step II) with an amount of the compound of formula (I), wherein the amount of the compound of formula (I) is sufficient to maintain the natural freshness and / or radiance of one or more or all fragrances of the formula Components (b) and / or (c) to reinforce and / or mask or reduce fatty, technical and / or metallic notes.
  • fragrances other than the compound of formula (I) in particular with a floral odor note, preferably jasmine, wherein preferably the one or more of the compound of formula (I) different fragrances is or are selected from the components (b) and / or (c) of a fragrance mixture according to the invention (as described herein).
  • fragrance or fragrances other than the compound of the formula (I) are selected from the constituents (b) and / or (c) of a fragrance mixture according to the invention.
  • DPG dipropylene glycol
  • DEP diethyl phthalate
  • TEC triethyl citrate
  • IPM isopropyl myristate
  • HEDIONE® (HC / 30) contains at least 30% by weight of the cis isomer and about 70% by weight of the trans isomer of methyl dihydrojasmonate.
  • perfume oils P1, P2, P3, P4 or P5 according to the invention from the above perfume oil examples 1 to 5 were each incorporated separately into the following formulations (products).
  • Trisodium citrate Tri Sodium Citrate
  • Example F11 Liquid detergent concentrate
  • Citric acid 1 0
  • 180g 1. Step in 700 g of ethanol are hydrogenated with 10 g of palladium 5% on A-carbon at 10 bar and 75 ° C. After completion of the reaction, the catalyst is filtered off and concentrated. The crude yield of 180g is distilled at a 40cm M.F.K. Yield 165g corresponds to 79.6% d. Th.
  • the product comprises the following isomers:

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne en particulier un mélange de parfums, de préférence une huile parfumée, comprenant les composants (a) (tricyclo[5.2.1.0]-décan-8-éthyléther) (I) ainsi que (b) un ou plusieurs parfums, ayant de préférence une note fleurie, dans le groupe constitué des alcools et des aldéhydes ayant une masse molaire de 210 g/mol ou moins et/ou (c) un ou plusieurs parfums dans le groupe constitué des cétones, des éthers et des esters ayant une masse molaire dans la plage de 190 g/mol à 250 g/mol. L'invention concerne en outre un procédé pour produire des mélanges de parfums selon l'invention, en particulier des huiles parfumées, des produits parfumés contenant un mélange parfumé selon l'invention, un procédé pour fabriquer des produits parfumés selon l'invention ainsi que l'utilisation du composé de formule (I) pour renforcer la fraîcheur et/ou la diffusion naturelles et/ou pour masquer ou atténuer les notes grasses, techniques et/ou métalliques d'un ou de plusieurs parfums différents du composé de formule (I).
EP17713214.9A 2017-03-21 2017-03-21 Mélanges de parfums contenant du tricyclo[5.2.1.0]-décan-8-éthyléther Pending EP3601509A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2017/056711 WO2018171872A1 (fr) 2017-03-21 2017-03-21 Mélanges de parfums contenant du tricyclo[5.2.1.0]-décan-8-éthyléther

Publications (1)

Publication Number Publication Date
EP3601509A1 true EP3601509A1 (fr) 2020-02-05

Family

ID=58410286

Family Applications (1)

Application Number Title Priority Date Filing Date
EP17713214.9A Pending EP3601509A1 (fr) 2017-03-21 2017-03-21 Mélanges de parfums contenant du tricyclo[5.2.1.0]-décan-8-éthyléther

Country Status (5)

Country Link
US (1) US10920170B2 (fr)
EP (1) EP3601509A1 (fr)
JP (1) JP7065873B2 (fr)
CN (1) CN110520513B (fr)
WO (1) WO2018171872A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2021012399A (es) 2019-04-12 2021-12-10 Ecolab Usa Inc Limpiador antimicrobiano multiuso y métodos de fabricación y uso de este.
CN114606030A (zh) * 2022-03-16 2022-06-10 金佳媛 一种利用废香料油生产燃料油的方法
CN115959973A (zh) * 2022-12-30 2023-04-14 广东希必达新材料科技有限公司 一种连续生产双环戊二烯乙二醇醚的方法

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2642519A1 (de) 1976-09-22 1978-03-23 Basf Ag Verfahren zur herstellung von tricyclo-eckige klammer auf 5.2.1.0 hoch 2.6 eckige klammer zu-dec-3-en- 9(8)-yl-alkyl- oder -alkenylaethern
DE3501888A1 (de) 1985-01-22 1986-07-24 Grau Aromatics GmbH & Co KG, 7070 Schwäbisch Gmünd Neue tricyclo (5.2.1.0(pfeil hoch)2(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)6(pfeil hoch))-decan-8-yl-ether, deren darstellung und verwendung als riechstoffe
US20030147937A1 (en) 2000-04-12 2003-08-07 Thomas Schwarz Use of compatible solutes as substances having free radical scavenging properties
SE0002960D0 (sv) 2000-08-21 2000-08-21 Eurotube Ab Engångs-smådjursfälla
DE10254872A1 (de) 2002-11-25 2004-06-03 Symrise Gmbh & Co. Kg Anthranilsäureamide und deren Derivate als kosmetische und pharmazeutische Wirkstoffe
FR2869621B1 (fr) * 2004-04-30 2008-10-17 Total France Sa Utilisation d'additifs pour ameliorer l'odeur de compositions d'hydrocarbures et compositions d'hydrocarbures comprenant de tels additifs
DE102004029239A1 (de) 2004-05-03 2005-12-01 Symrise Gmbh & Co. Kg Benyliden-β-dicarbonylverbindungen als neue UV-Absorber
US9987217B2 (en) 2004-06-18 2018-06-05 Symrise Ag Blackberry extract
DE102004038485A1 (de) 2004-08-07 2006-02-23 Symrise Gmbh & Co. Kg alpha-Benzoyl-zimtsäurenitrile als neue UV-Absorber
AU2005298653A1 (en) 2004-10-25 2006-05-04 Symrise Gmbh & Co. Kg Use of glycosylated flavanones for the browning of skin or hair
ATE425732T1 (de) 2004-11-22 2009-04-15 Symrise Gmbh & Co Kg Formulierungen mit ceramiden und/oder pseudoceramiden und (alpha-)bisabolol zur behandlung von hautschaden
US8241681B2 (en) 2005-10-14 2012-08-14 Symrise Ag Synergistic mixtures of bisabolol and ginger extract
DE102005056890A1 (de) 2005-11-28 2007-05-31 Institut für Umweltmedizinische Forschung gGmbH Kosmetisches Verfahren zur Beeinflussung der Melaninbildung in der Haut
WO2007110415A2 (fr) 2006-03-27 2007-10-04 Symrise Gmbh & Co. Kg Utilisation de trimères diacétyliques et formulations cosmétiques ou thérapeutiques contenant ces composés
ES2421191T3 (es) 2006-05-03 2013-08-29 Symrise Ag Antagonistas del receptor de Ah
DE102006043587A1 (de) 2006-09-16 2008-03-27 Symrise Gmbh & Co. Kg 2-Methyl-2-alkenyl-substituierte 1,3-Dioxane als Riechstoffe
EP1915982A1 (fr) 2006-10-20 2008-04-30 Symrise GmbH & Co. KG Utilisation du 1,2-décanediol pour réduire la concentration du sébum et/ou pour aider à la pénétration des actives dans des régions de la peau, et des compositions cosmétiques et/ou dermatologiques comprenant du 1,2-décanediol
EP1923041A1 (fr) 2006-10-20 2008-05-21 Symrise GmbH & Co. KG Utilisation des C10-C14 alcane-diols pour la préparation d'une composition pour la prophylaxe et/ou le traitement des pellicules induites par Malassezia, ainsi que des compositions comprenant des C10-C14 alcane-diols
DE102006050398A1 (de) 2006-10-20 2008-04-24 Henkel Kgaa Kosmetisches Mittel enthaltend Purin und/oder Purinderivat und Taurin

Also Published As

Publication number Publication date
US10920170B2 (en) 2021-02-16
CN110520513A (zh) 2019-11-29
WO2018171872A1 (fr) 2018-09-27
JP7065873B2 (ja) 2022-05-12
JP2020514515A (ja) 2020-05-21
CN110520513B (zh) 2024-01-09
US20200063063A1 (en) 2020-02-27

Similar Documents

Publication Publication Date Title
EP2474301B1 (fr) Mélanges de parfum comprenant du cyclopent-2-ényl-éthylester d'acide acétique
EP2568035B1 (fr) Melanges de parfums comprenant certains ethers de methyle d'isolongifolenyle
EP3279300B1 (fr) Composition parfumante
EP2803666B1 (fr) Acétals et cétals cycliques et leur utilisation en tant que parfum
EP2184339B1 (fr) Mélanges de parfum comprenant de l'Isolongifolanol et du Moschus
EP2287158B1 (fr) Parfum d'ambre à base de 9-Methanoazuleno(5,6-d)-1,3-dioxoles
WO2012160189A1 (fr) Alcools terpéniques destinés à être utilisés dans des compositions de parfum et produits parfumés
EP3601509A1 (fr) Mélanges de parfums contenant du tricyclo[5.2.1.0]-décan-8-éthyléther
KR20150061640A (ko) 향료 조성물
AT525502B1 (de) Mischungen enthaltend enantiomerenreines Ambrocenide®
EP3362428B1 (fr) Nouveaux composés d'octahydro-indènyle propanal
EP1942178B1 (fr) Mélanges de 3-(4-Méthyl-cyclohex-3-ényl)-butyraldéhyde et 2,6-Diméthyl-7-octén-2-ol
DE602004001076T2 (de) Riechstoffverbindungen
EP3723709B1 (fr) MÉLANGES DE PARFUMS COMPRENANT DU
8,8-DIMÉTHYLE-6,10-DIOXASPIRO[4,5]DÉCANE
EP4045490A1 (fr) Nouveaux monothiocétals aromatiques en tant que substances odorantes
DE602005005206T2 (de) Ungesättigte ether als parfümstoffe
EP3658655B1 (fr) Composés organiques
US7384897B1 (en) Cyclopropanecarbonitrile analogues and their use in perfume compositions
US20140323768A1 (en) 3-methyl-6-cyclohexadecen-1-one and its use in perfume compositions
JP2000044506A (ja) 新規化合物および香料組成物
MXPA06002669A (es) 4-metildec-4-en-3-ol y composicion de fragancia.

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20191021

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20230626