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EP0858498B1 - Nitrile - Google Patents

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Publication number
EP0858498B1
EP0858498B1 EP96934289A EP96934289A EP0858498B1 EP 0858498 B1 EP0858498 B1 EP 0858498B1 EP 96934289 A EP96934289 A EP 96934289A EP 96934289 A EP96934289 A EP 96934289A EP 0858498 B1 EP0858498 B1 EP 0858498B1
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EP
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Prior art keywords
oil
perfume
acetate
fragrance
phenyl acetonitrile
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Expired - Lifetime
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EP96934289A
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German (de)
French (fr)
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EP0858498A1 (en
Inventor
Mario Pesaro
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Givaudan SA
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Givaudan SA
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    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C11B9/0065—Nitriles

Definitions

  • the invention accordingly relates to fragrance compositions with a I content and the use of I as a fragrance.
  • the smell of I can be floral-rosy, green, metallic, on geranium remembering, being characterized.
  • Rosacetol trichloromethyl phenyl carbinyl acetate
  • I is ideal for use in the Detergent industry, e.g. as a fragrance in detergents, Fabric softener, e.g., but also as a fragrance in cosmetics, e.g. in Shampoos, soaps, etc., especially as a replacement for rosacetol.
  • the compound I When used as a fragrance, the compound I use within wide limits, for example of approx. 0.1 (Detergents) up to approx. 30 percent by weight (alcoholic solutions) in Compositions can do without these values however Limit values should represent, since the experienced perfumer also with even lower concentrations achieve effects or with still higher doses can build up new complexes.
  • the preferred concentrations range between approximately 1 and approximately 20 Percent by weight.
  • the prepared with the compounds I. Compositions can be used for all types of perfumed Use consumer goods (Eaux de Cologne, Eaux de Toilette, Extraits, lotions, creams, shampoos, soaps, ointments, powder, Deodorants, detergents, fabric finishers, bleaches, Fabric softener, etc.
  • the compound I can accordingly be used in the production of compositions and - as the above composition shows - using a wide range of known fragrances or mixtures of fragrances.
  • the above-mentioned known fragrances or mixtures of fragrances can be used in a known manner (as the perfumer), such as from WA Poucher, Perfumes, Cosmetics and Soaps 2 , 7, edition, Chapman and Hall, London, 1974 emerges.
  • composition Even after 24 hours, the composition is much easier, fresher; it is very suitable for men's colognes of a modern character.
  • Perfume composition towards hawthorn Parts by weight Terpineol 250 ⁇ -hexyl cinnamaldehyde 100 Phenylethyl alcohol 140 Hydroxycitronellal 100 Anisaldehyde ex anethole 60 Heliotropin 50 Linalool 40 Benzyl acetate 30th Geraniol 30th Bergamot oil 30th ⁇ -Jonon 20th Ambrette musk 20th Citronellol 10th Ethylene brassylate 10th Methyl acetophenone 10th Coumarin 10th Pure indole 5 Geranyl acetate 5 Phenylacetaldehyde 5 Civette absolute 10% in propylene glycol 5 Ylang-ylang oil 10th Isoeugenol 5 Phenylacetaldehyde dimethylacetal 5 950

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Von V.J. Harding und W.N. Haworth wird in J.Chem.Soc. (1910), 486-498 das Cyclohex-1-en-yl-phenylacetonitril C6H5CH(CN)-C6H9 als Produkt der alkalischen Kondensation von Phenylacetonitril und Cyclohexanon beschrieben.VJ Harding and WN Haworth in J.Chem.Soc. (1910), 486-498 describes the cyclohex-1-en-yl-phenylacetonitrile C 6 H 5 CH (CN) -C 6 H 9 as the product of the alkaline condensation of phenylacetonitrile and cyclohexanone.

Es hat sich später aber herausgestellt, dass sich bei dem Reaktionsprodukt in Tat und Wahrheit um das Cyclohexyliden-phenylacetonitril C6H5C(CN)=C6H10 (I) handelt, D.E. Whyte, A. Cope, JACS 65 (1943), 1999-2000 und S.F. Birch, G.A.R. Kon, J. Chem. Soc. 123 (1923), 2442-2446.It was later found, however, that the reaction product is in fact the cyclohexylidene-phenylacetonitrile C 6 H 5 C (CN) = C 6 H 10 (I), DE Whyte, A. Cope, JACS 65 (1943 ), 1999-2000 and SF Birch, GAR Kon, J. Chem. Soc. 123 (1923), 2442-2446.

Harding und Haworth beschreiben das von ihnen erhaltene Produkt bloss als farbloses Oel mit angenehmem etherischem Geruch. Die späteren Autoren machen hierüber überhaupt keine Angaben.Harding and Haworth describe the product they received just as a colorless oil with a pleasant ethereal smell. The later ones Authors do not provide any information about this.

Dass sich hinter dieser kursorischen, zudem recht ungenauen, unspezifischen Geruchsbeschreibung ein Riechstoff mit äusserst wertvollen Eigenschaften und - wie anfangs ausgeführt - mannigfaltigen Einsatzmöglichkeiten versteckte, ist überraschend.That behind this cursory, also quite imprecise, unspecific description of smell a fragrance with extremely valuable Properties and - as stated at the beginning - various possible uses hidden is surprising.

Die Erfindung betrifft demgemäss Riechstoffkompositionen mit einem Gehalt an I und die Verwendung von I als Riechstoff.The invention accordingly relates to fragrance compositions with a I content and the use of I as a fragrance.

Der Geruch von I kann als blumig-rosig, grün, metallisch, an Geranium erinnernd, charakterisiert werden.The smell of I can be floral-rosy, green, metallic, on geranium remembering, being characterized.

Aufgrund olfaktorischer Untersuchungen hat sich ferner ergeben, dass sich I, insbesondere aufgrund seiner Rosen- und Geraniumnoten überraschenderweise ausgezeichnet als Ersatz für Rosacetol eignet. Based on olfactory investigations, it also emerged that himself I, especially because of its rose and geranium notes Surprisingly, it is an excellent substitute for rosacetol.

Rosacetol (Trichlor-methyl-phenyl-carbinyl-acetat) ist ein aufgrund seiner Rosen- und Geraniumnoten sehr geschätzter Riechstoff, dessen Verwendung in letzter Zeit aus ökologischen Gründen (Chlorgehalt) aber mehr und mehr zurückgeht.Rosacetol (trichloromethyl phenyl carbinyl acetate) is a much appreciated due to its rose and geranium notes Fragrance, its use lately from ecological Reasons (chlorine content) but declines more and more.

Es hat sich ferner herausgestellt, dass (I) ausserordentlich säure- und alkalistabil ist, und dass sich (I) durch ausgezeichnete Substantivität auszeichnet. Bezüglich Substantivität ist I dem Rosacetol sogar ganz deutlich überlegen. Dasselbe gilt für die Langlebigkeit.It has also been found that (I) and is alkali stable, and that (I) is distinguished by excellent Distinguished substantivity. Regarding substantivity, I is rosacetol even consider it clearly. The same applies to longevity.

Unter Substantivität wird die Haftung eines Riechstoffs, z.B. auf Textilien, Haut und Haar nach dem Waschvorgang verstanden.The liability of a fragrance, e.g. on Understand textiles, skin and hair after washing.

Demzufolge eignet sich I hervorragend für die Verwendung in der Waschmittelindustrie, z.B. als Riechstoff in Detergentien, Weichspülern, zsw., aber auch als Riechstoff in der Kosmetik, z.B. in Shampoos, Seifen, usw., insbesondere als Ersatz für Rosacetol.As a result, I is ideal for use in the Detergent industry, e.g. as a fragrance in detergents, Fabric softener, e.g., but also as a fragrance in cosmetics, e.g. in Shampoos, soaps, etc., especially as a replacement for rosacetol.

Aufgrund der obenerwähnten wertvollen olfaktorischen Eigenschaften eignet sich die Verbindung I als Riechstoff, und zwar insbesondere in Kombination mit der gängigen heutzutage zur Verfügung stehenden umfangreichen Palette von natürlichen und synthetischen Riechstoffen, zur Kreaktion von Parfüm-Kompositionen, welche ihre Anwendung in allen üblichen Applikations-Segmenten finden können. Beispiele der zahlreichen bekannten Riechstoffingredientien natürlichen oder synthetischen Ursprungs, wobei die Palette der natürlichen Rohstoffe sowohl leicht- als auch mittel- und schwerflüchtige Komponenten, und diejenige der Synthetika Vertreter aus etlichen Stoffklassen umfassen kann, sind:

  • Naturprodukte, wie Baummoos-Absolue, Basilikumöl, Agrumenöle (wie Bergamotteöl, Mandarinenöl, usw.), Mastix-Absolue, Myrtenöl, Palmarosaöl, Patchouliöl, Petitgrainöl, Wermutöl, Lavendelöl, Rosenöl, Jasminöl, Ylang-Ylangöl, Sandelholzöl,
  • Alkohole, wie Farnesol, Geraniol, Linalool, Nerol, Phenyläthyl-lkohol, Rhodinol, Zimtalkohol, cis-3-Hexenol, Menthol, α-Terpineol, Sandela (3-Isocamphyl-(5)-cyclohexanol),
  • Aldehyde, wie Citral, α-Hexylzimtaldehyd, Hydroxycitronellal, Lilial® (p-tert.Butyl-α-methyl-dihydrozimtaldehyd), Methylnonylacetaldehyd, Phenylacetaldehyd, Anisaldehyd, Vanillin,
  • Ketone, wie Allyljonon, α-Jonon, β-Jonon, Isoraldein (Isomethyl-α-jonon), Verbenone, Nootkaton, Geranylaceton,
  • Ester, wie Allyl-phenoxyacetat, Benzyl-salicylat, Cinnamylpropionat, Citronellyl-acetat, Decylacetat, Dimethylbenzylcarbinyl-acetat, Aethyl-acetoacetat, Aethyl-acetylacetat, cis-3-Hexenyl-isobutyrat, Linalylacetat, Methyl-dihydrojasmonat, Styrallylacetat, Vetiverylacetat, Benzylacetat, cis-3-Hexenylsalicylat, Geranylacetat, usw.
  • Lactone, wie γ-Undecalacton, δ-Decalacton, Pentadecan-15-olid,
  • verschiedene, in der Parfümerie oft benützte Komponenten, wie Indol, p-Menthan-8-thiol-3-on, Methyleugenol, Eugenol, Anethol, etc.
Because of the above-mentioned valuable olfactory properties, the compound I is suitable as a fragrance, in particular in combination with the wide range of natural and synthetic fragrances currently available, for the reaction of perfume compositions which are used in all common application segments can find. Examples of the numerous known fragrance ingredients of natural or synthetic origin, where the range of natural raw materials includes both volatile, medium and low volatile components, and that of synthetics can include representatives from a number of substance classes:
  • Natural products, such as tree moss absolute, basil oil, agricultural oils (such as bergamot oil, mandarin oil, etc.), mastic absolute, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil, wormwood oil, lavender oil, rose oil, jasmine oil, ylang-ylang oil, sandalwood oil,
  • Alcohols, such as farnesol, geraniol, linalool, nerol, phenylethyl alcohol, rhodinol, cinnamon alcohol, cis-3-hexenol, menthol, α-terpineol, Sandela (3-isocamphyl- (5) -cyclohexanol),
  • Aldehydes, such as citral, α-hexylcinnamaldehyde, hydroxycitronellal, Lilial® (p-tert-butyl-α-methyl-dihydrocinnamaldehyde), methylnonylacetaldehyde, phenylacetaldehyde, anisaldehyde, vanillin,
  • Ketones, such as allyl ionone, α-ionone, β-ionone, isoraldein (isomethyl-α-ionone), verbenone, nootkatone, geranylacetone,
  • Esters, such as allyl phenoxyacetate, benzyl salicylate, cinnamyl propionate, citronellyl acetate, decyl acetate, dimethylbenzylcarbinyl acetate, ethyl acetoacetate, ethyl acetylacetate, cis-3-hexenyl isobutyrate, linalyl acetate, methyl, vydroxylacetyl acetate , cis-3-hexenyl salicylate, geranyl acetate, etc.
  • Lactones , such as γ-undecalactone, δ-decalactone, pentadecan-15-olide,
  • various components often used in perfumery, such as indole, p-menthan-8-thiol-3-one, methyleugenol, eugenol, anethole, etc.

Die unter Verwendung von Verbindungen I hergestellten Riechstoffkompositionen, insbesondere solcher blumiger, blumigwürziger, blumig-fruchtiger und blumig-orientalischer Richtung, bestechen besonders durch ihre Originalität.Those made using Compounds I Fragrance compositions, especially those with a floral, spicy floral floral-fruity and floral-oriental direction, impress with their originality.

Bei ihrer Verwendung als Riechstoff lässt sich die Verbindung I in weiten Grenzen einsetzen, die beispielsweise von ca. 0,1 (Detergentien) bis ca. 30 Gewichtsprozent (alkoholische Lösungen) in Kompositionen reichen können, ohne dass diese Werte jedoch Grenzwerte darstellen sollen, da der erfahrene Parfümeur auch mit noch geringeren Konzentrationen Effekte erzielen oder aber mit noch höheren Dosierungen neuartige Komplexe aufbauen kann. Die bevorzugten Konzentrationen bewegen sich zwischen ca. 1 und ca. 20 Gewichtsprozent. Die mit den Verbindungen I hergestellten Kompositionen lassen sich für alle Arten von parfümierten Verbrauchsgütern einsetzen (Eaux de Cologne, Eaux de Toilette, Extraits, Lotionen, Crèmes, Shampoos, Seifen, Salben, Puder, Desodorantien, Detergentien, Gewebeveredler, Bleichmittel, Weichspüler für Textilien, usw. When used as a fragrance, the compound I use within wide limits, for example of approx. 0.1 (Detergents) up to approx. 30 percent by weight (alcoholic solutions) in Compositions can do without these values however Limit values should represent, since the experienced perfumer also with even lower concentrations achieve effects or with still higher doses can build up new complexes. The preferred concentrations range between approximately 1 and approximately 20 Percent by weight. The prepared with the compounds I. Compositions can be used for all types of perfumed Use consumer goods (Eaux de Cologne, Eaux de Toilette, Extraits, lotions, creams, shampoos, soaps, ointments, powder, Deodorants, detergents, fabric finishers, bleaches, Fabric softener, etc.

Die Verbindung I kann demgemäss bei der Herstellung von Kompositionen und - wie obige Zusammenstellung zeigt - unter Verwendung einer breiten Palette bekannter Riechstoffe bzw. Riechstoffgemische verwendet werden. Bei der Herstellung solcher Kompositionen können die oben aufgeführten bekannten Riechstoffe bzw. Riechstoffgemische nach (dem Parfümeur) bekannter Art und Weise verwendet werden, wie dies z.B. aus W.A. Poucher, Perfumes, Cosmetics and Soaps 2, 7, Auflage, Chapman und Hall, London, 1974 hervorgeht.The compound I can accordingly be used in the production of compositions and - as the above composition shows - using a wide range of known fragrances or mixtures of fragrances. In the production of such compositions, the above-mentioned known fragrances or mixtures of fragrances can be used in a known manner (as the perfumer), such as from WA Poucher, Perfumes, Cosmetics and Soaps 2 , 7, edition, Chapman and Hall, London, 1974 emerges.

Beispiel 1example 1

Chypre KompositionChypre composition GewichtsteileParts by weight BenzylsalicylatBenzyl salicylate 100100 Ambrette-moschusAmbrette musk 100100 HydroxycitronellalHydroxycitronellal 100100 Sandela® GivaudanSandela® Givaudan 100100 VetivenylacetatVetivenyl acetate 5050 PatchouliölPatchouli oil 5050 Ylang-Ylang-ölYlang-ylang oil 4040 Methylnonylacetaldehyd 10% in PropylenglykolMethylnonylacetaldehyde 10% in propylene glycol 4040 Galbanumöl 10% in AlkoholGalbanum oil 10% in alcohol 4040 MelissenölMelissa oil 3030th Eichenmoos löslichOak moss soluble 3030th StyrallylacetatStyrallyl acetate 3030th ZimtalkoholCinnamon alcohol 2020th Aldehyd C-11 (10-Undecenal) 10% in PropylenglykolAldehyde C-11 (10-undecenal) 10% in propylene glycol 2020th VernaldehydVernaldehyde 2020th Eugenol extraEugenol extra 2020th MajoranölMarjoram oil 1010th Weihrauch-resinoidIncense resinoid 1010th γ-Undecalakton 10% in Propylenglykolγ-undecalactone 10% in propylene glycol 1010th HeliotropinHeliotropin 3030th Rhodinol extraRhodinol extra 5050 900900

Gibt man zu dieser etwas schweren Chypre-Komposition 100 Teile I, so wird diese sehr angenehm frisch in Richtung Citrus verändert. Die Komposition wirkt nun viel leichter und viel moderner.If you add 100 pieces to this somewhat heavy chypre composition I, this is changed very pleasantly fresh towards Citrus. The composition now looks much lighter and much more modern.

Auch nach 24 Stunden ist die Komposition noch viel leichter, frischer; sie ist sehr geeignet für Herren-Colognes moderner Prägung.Even after 24 hours, the composition is much easier, fresher; it is very suitable for men's colognes of a modern character.

Beispiel 2Example 2

Parfumerie-Komposition in Richtung HyacinthePerfume composition towards Hyacinthe GewichtsteileParts by weight PhenyläthylalkoholPhenylethyl alcohol 200200 HydroxycitronellalHydroxycitronellal 100100 ZimtalkoholCinnamon alcohol 100100 PhenyläthylisobutyratPhenylethyl isobutyrate 8080 PhenylpropylalkoholPhenylpropyl alcohol 6060 BenzylaetatBenzyl acetate 5050 Baccartol® Givaudan (Rosenbase auf Basis Citronelle-öl/aceton-kondensationsproduktBaccartol® Givaudan (rose base based on citronelle oil / acetone condensation product 4040 PhenyläthylformiatPhenylethyl formate 4040 CitronellolCitronellol 3030th EugenolEugenol 2020th Galbanum-ölGalbanum oil 2020th Phenylacetaldehyd 10% in PropylenglykolPhenylacetaldehyde 10% in propylene glycol 2020th Maltol 1% in PropylenglykolMaltol 1% in propylene glycol 2020th Dimethylacetat des HydratropaldehydsDimethyl acetate of hydratropaldehyde 1010th GeranylacetatGeranyl acetate 1010th 800800

Gibt man zu dieser Hyacinthen-Base 200 Teile I, so wirkt sie alsbald viel typischer Richtung Hyacinthe. I verbindet sich vorteilhaft mit den Komponenten, welche die grüne Note bilden, indem sie diese wesentlich weicher erscheinen lässt. If you add 200 parts I to this hyacinth base, it works soon much more typical direction Hyacinthe. I combines advantageously with the components that make up the green note by makes it appear much softer.

Beispiel 3Example 3

Parfumerie-Komposition in Richtung WeissdornPerfume composition towards hawthorn GewichtsteileParts by weight TerpineolTerpineol 250250 α-Hexylzimtaldehydα-hexyl cinnamaldehyde 100100 PhenyläthylalkoholPhenylethyl alcohol 140140 HydroxycitronellalHydroxycitronellal 100100 Anisaldehyd ex AnetholAnisaldehyde ex anethole 6060 HeliotropinHeliotropin 5050 LinaloolLinalool 4040 BenzylacetatBenzyl acetate 3030th GeraniolGeraniol 3030th Bergamotte-ölBergamot oil 3030th α-Jononα-Jonon 2020th Ambrette-moschusAmbrette musk 2020th CitronellolCitronellol 1010th Aethylen-brassylatEthylene brassylate 1010th MethylacetophenonMethyl acetophenone 1010th CoumarinCoumarin 1010th Indol purPure indole 55 GeranylacetatGeranyl acetate 55 PhenylacetaldehydPhenylacetaldehyde 55 Civette absolue 10% in PropylenglykolCivette absolute 10% in propylene glycol 55 Ylang-Ylang-ölYlang-ylang oil 1010th IsoeugenolIsoeugenol 55 Phenylacetaldehyd-dimethylacetalPhenylacetaldehyde dimethylacetal 55 950950

Gibt man zu dieser blumig-süssen Komposition 50 Teile I, so wird deren pudrige Note sehr schön in eine blumig-rosigen Variante eingekleidet. Eine angenehm fliedrige Note tritt verstärkt hervor. Ausserdem kommt eine Honig-note zur Geltung, welche der Base mehr Diffusion verleiht. If you add 50 parts I to this flowery-sweet composition, you will their powdery note very beautiful in a floral-rosy variant dressed. A pleasantly gentle note emerges. In addition, a honey note comes into play, which is the base gives more diffusion.

Beispiel 4Example 4

Parfumerie-Komposition in Richtung GardeniaPerfume composition towards Gardenia GewichtsteileParts by weight HydroxycitronellalHydroxycitronellal 120120 BenzylacetatBenzyl acetate 100100 Bergamotte-ölBergamot oil 100100 α-Jononα-Jonon 100100 Neroli-ölNeroli oil 7070 StyrallylacetatStyrallyl acetate 7070 LinaloolLinalool 7070 HeliotropinHeliotropin 5050 Ylang-Ylang-ölYlang-ylang oil 5050 Keton-moschus (4-tert.Butyl-3,5-dinitro-2,6-dimethyl-acetophenon)Ketone musk (4-tert-butyl-3,5-dinitro-2,6-dimethyl-acetophenone) 5050 IsoeugenolIsoeugenol 3030th Jasmin-ölJasmine oil 3030th α-Hexylzimtaldehydα-hexyl cinnamaldehyde 3030th Ambrette-moschusAmbrette musk 3030th Phenylacetaldehyd 50% in PropylenglykolPhenylacetaldehyde 50% in propylene glycol 1515 Civette absolue 10% in PropylenglykolCivette absolute 10% in propylene glycol 55 Aldehyd C-10 (n-Decyl-) 10% in PropylenglykolAldehyde C-10 (n-decyl) 10% in propylene glycol 55 Orangenöl kalifornischCalifornian orange oil 55 930930

Gibt man zu dieser blumigen Base in Richtung Gardenia 70 Teile I, so erhält diese eine verstärkende Honig-Note, welche die Base viel abgerundeter erscheinen lässt. Durch I wirkt die Base viel harmonischer. I bildet einen ausgesprochen ausgleichenden Faktor in der Komposition.Add 70 pieces to this flowery base towards Gardenia I, this gives it a strengthening honey note, which the base a lot makes it appear more rounded. I makes the base work a lot more harmonious. I is a very balancing factor in the composition.

Claims (10)

  1. Perfume compositions characterised by a content of cyclohexylidene phenyl acetonitrile.
  2. Acid-resistant and alkali-resistant perfume compositions according to claim 1.
  3. Perfume compositions according to claim 1 for use in the cosmetics industry.
  4. Perfume compositions according to claim 1 for use in the detergent industry.
  5. Perfume compositions according to claim 1 with rose notes and/or geranium notes.
  6. Use of cyclohexylidene phenyl acetonitrile as a perfume.
  7. Use of cyclohexylidene phenyl acetonitrile as a perfume resistant to acids and alkalis.
  8. Use of cyclohexylidene phenyl acetonitrile as a perfume for the detergent industry.
  9. Use of cyclohexylidene phenyl acetonitrile as a perfume for the cosmetics industry.
  10. Use of cyclohexylidene phenyl acetonitrile as a perfume with rose notes and/or geranium notes.
EP96934289A 1995-11-01 1996-10-24 Nitrile Expired - Lifetime EP0858498B1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH309395 1995-11-01
CH3093/95 1995-11-01
CH309395 1995-11-01
PCT/CH1996/000377 WO1997016512A1 (en) 1995-11-01 1996-10-24 Nitrile

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EP0858498A1 EP0858498A1 (en) 1998-08-19
EP0858498B1 true EP0858498B1 (en) 2001-09-12

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JP (1) JP3802068B2 (en)
DE (1) DE59607690D1 (en)
ES (1) ES2162101T3 (en)
WO (1) WO1997016512A1 (en)

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WO2008055372A1 (en) * 2006-11-07 2008-05-15 Givaudan Sa Malodor counteracting compositions

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EP1269982A1 (en) * 2001-06-30 2003-01-02 Givaudan SA Fragrance and flavour compositions
ES2309662T3 (en) * 2004-09-16 2008-12-16 Firmenich S.A. DERIVATIVES OF NITRILE AS INGREDIENTS OF PERFUMERIA.
GB0512284D0 (en) * 2005-06-16 2005-07-27 Givaudan Sa Organic compounds
GB0518558D0 (en) * 2005-09-12 2005-10-19 Givaudan Sa Improvements in or related to organic compounds
US7390772B2 (en) * 2006-05-18 2008-06-24 International Flavor & Fragrances Inc. 1-phenyl-spiro[2.5]octane-1-carbonitrile analogues their use in fragrance formulations
GB201021050D0 (en) * 2010-12-13 2011-01-26 Givaudan Sa Moc compositions
GB201407383D0 (en) * 2014-04-28 2014-06-11 Givaudan Sa Improvements in or relating to organic compounds
ES2704076T3 (en) * 2014-12-08 2019-03-14 Firmenich & Cie Aliphatic nitrile with pink smell

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US3408396A (en) * 1965-10-22 1968-10-29 Colgate Palmolive Co alpha-cyclohexyl-3, 4-disubstituted-phenyl acetamides
DE3139358C2 (en) * 1981-10-02 1984-06-07 Dragoco Gerberding & Co Gmbh, 3450 Holzminden Use of 1,1-di (C 1 -C 6 -alkyl) -2-phenyl-ethane derivatives as odoriferous substances

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008055372A1 (en) * 2006-11-07 2008-05-15 Givaudan Sa Malodor counteracting compositions

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JP3802068B2 (en) 2006-07-26
JP2000514104A (en) 2000-10-24
ES2162101T3 (en) 2001-12-16
US6069125A (en) 2000-05-30
WO1997016512A1 (en) 1997-05-09
EP0858498A1 (en) 1998-08-19
DE59607690D1 (en) 2001-10-18

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