EP0858498A1 - Nitrile - Google Patents

Nitrile

Info

Publication number
EP0858498A1
EP0858498A1 EP96934289A EP96934289A EP0858498A1 EP 0858498 A1 EP0858498 A1 EP 0858498A1 EP 96934289 A EP96934289 A EP 96934289A EP 96934289 A EP96934289 A EP 96934289A EP 0858498 A1 EP0858498 A1 EP 0858498A1
Authority
EP
European Patent Office
Prior art keywords
fragrance
oil
phenylacetonitrile
cyclohexylidene
acetate
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.)
Granted
Application number
EP96934289A
Other languages
German (de)
French (fr)
Other versions
EP0858498B1 (en
Inventor
Mario Pesaro
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.)
Givaudan SA
Original Assignee
Givaudan Roure International SA
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Filing date
Publication date
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Publication of EP0858498A1 publication Critical patent/EP0858498A1/en
Application granted granted Critical
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Anticipated expiration legal-status Critical
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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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • C11B9/0065—Nitriles

Definitions

  • the invention accordingly relates to the compound I as a fragrance, fragrance compositions containing I and the use of I as a fragrance.
  • the smell of I can be characterized as floral-rosy, green, metallic, reminiscent of geranium.
  • Rosacetol is suitable. Rosacetol (trichloromethyl-phenyl-carbinyl-acetate) is a highly valued fragrance due to its rose and geranium notes, the use of which has been declining more and more recently for ecological reasons (chlorine content).
  • fragrance e.g. understood on textiles, skin and hair after washing.
  • I is ideal for use in the detergent industry, e.g. as a fragrance in detergents, fabric softeners, etc., but also as a fragrance in cosmetics, e.g. in shampoos, soaps, etc., especially as a replacement for rosacetol.
  • 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 can be used in all common application segments.
  • 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, ⁇ -terpineol, Sandela (3-isocamphyl- (5) -cyclohexanol), Aldehvde.
  • citral such as citral, ⁇ -hexylcinnamaldehyde, hydroxy citronellal, LiUal® (p-tert-butyl- ⁇ -methyl-dihydrocinnamaldehyde), methylnonylacetaldehyde, phenylacetaldehyde, anisaldehyde, vanillin,
  • ketones such as allyl Jonon, ⁇ -Jonon, ⁇ -Jonon, Isoraldein (Isomethyl- ⁇ -jonoon), Verbenone, Nootkaton, 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 ⁇ -undecalactone, ⁇ -decalactone, pentadecan-15-olide,
  • perfumery various components often used in perfumery, such as indole, p-menthan-8-thiol-3-one, methyleugenol, eugenol, anethole, etc.
  • fragrance compositions produced using compounds I are particularly spectacular due to their originality.
  • the compound I When used as a fragrance, the compound I can be used within wide limits, which can range, for example, from about 0.1 (detergents) to about 30 percent by weight (alcoholic solutions) in compositions without these values being intended to represent limit values, however the experienced perfumer can achieve effects with even lower concentrations or build new complexes with even higher doses.
  • the preferred concentrations range between about 1 and about 20 percent by weight.
  • the compositions prepared with the compounds I can be perfumed for all types
  • 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 manner known to (the perfumer), as can be seen, for example, from WA. Poucher, Perfumes, Cosmetics and Soaps 2_, 7th edition, Chapman and Hall, London, 1974.
  • composition Even after 24 hours, the composition is much lighter, fresher; it is very suitable for men's colognes of a modern character.
  • Baccartol® Givaudan (rose base based on citronelle oil / acetone condensation product 40
  • Ketone Musk (4-tert-butyl-3,5-dinitro-2,6-dimethyl-acetophenone) 50

Abstract

The invention relates to the use of cyclohexylidene phenyl acetonitrile as an odoriferous substance.

Description

Nitril Nitrile
Von V.J. Harding und W.N. Haworth wird in J.Chem.Soc. (1910), 486-498 das Cyclohex-1-en-yl-phenylacetonitril CβHsCHtCJND-CβHg als Produkt der alkalischen Kondensation von Phenylacetonitril und Cyclohexanon beschrieben.By V.J. Harding and W.N. Haworth is described in J.Chem.Soc. (1910), 486-498 described the cyclohex-1-en-yl-phenylacetonitrile CβHsCHtCJND-CβHg 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)=C6Hιo (I) handelt, D.E. Whyte, A. Cope, JACS ßδ (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 C6H 5 C (CN) = C 6 Hιo (I), DE Whyte, A. Cope, JACS ßδ (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 etherischen Geruch. Die späteren Autoren machen hierüber überhaupt keine Angaben.Harding and Haworth describe the product they received merely as a colorless oil with a pleasant ethereal smell. The later authors make no statements at all about this.
Dass sich hinter dieser kursorischen, zudem äusserst ungenauen, unspezifischen Geruchsbeschreibung ein Riechstoff mit äusserst wertvollen Eigenschaften und - wie unten ausgeführt - mannigfaltigen Einsatzmoglichkeiten versteckte, ist überraschend.It is surprising that there was a fragrance with extremely valuable properties and - as explained below - hiding behind this cursory, also extremely imprecise, unspecific olfactory description.
Die Erfindung betrifft demgemäss die Verbindung I als Riechstoff, Riechstoffkompositionen mit einem Gehalt an I und die Verwendung von I als Riechstoff.The invention accordingly relates to the compound I as a fragrance, fragrance compositions containing I 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 characterized as floral-rosy, green, metallic, reminiscent of geranium.
Aufgrund olfaktorischer Untersuchungen hat sich ferner ergeben, dass sich I, insbesondere aufgrund seiner Rosen- und Geraniumnoten überraschenderweise ausgezeichnet als Ersatz fürOn the basis of olfactory investigations, it has further emerged that I, in particular due to its rose and geranium notes, surprisingly excels as a replacement for
Rosacetol eignet. 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 is suitable. Rosacetol (trichloromethyl-phenyl-carbinyl-acetate) is a highly valued fragrance due to its rose and geranium notes, the use of which has been declining more and more recently for ecological reasons (chlorine content).
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 deutüch überlegen. Dasselbe gilt für die Langlebigkeit.It has also been found that (I) is extremely acid and alkali stable and that (I) is characterized by excellent substantivity. In terms of substantivity, I is even clearly superior to rosacetol. 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. understood on 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 softeners, etc., but also as a fragrance in cosmetics, e.g. in shampoos, soaps, etc., especially as a replacement for rosacetol.
Aufgrund der obenerwähnten wertvollen olfaktorischenBecause of the above-mentioned valuable olfactory
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 Parfum-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: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 can be used in all common application segments. 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:
Naturprodukte, wie Baummoos-Absolue, Basilikumöl, Agrumenöle (wie Bergamotteöl, Mandarinenöl, usw.), Mastix- Absolue, Myrtenöl, Palmarosaöl, Patchouliöl, Petitgrainöl, Wermutöl, Lavendelöl, Rosenöl, Jasminöl, Ylang-Ylangöl, Sandelholzöl,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,
Alkohole, wie Farnesol, Geraniol, Linalool, Nerol, Phenyläthyl- lkohol, Rhodinol, Zimtalkohol, cis-3-Hexenol, Menthol, α- Terpineol, Sandela (3-Isocamphyl-(5)-cyclohexanol), Aldehvde. wie Citral, α-Hexylzimtaldehyd, Hydroxy citronellal, LiUal® (p-tert.Butyl-α-methyl-dihydrozimtaldehyd), Methylnonylacetaldehyd, Phenylacetaldehyd, Anisaldehyd, Vanillin,Alcohols, such as farnesol, geraniol, linalool, nerol, phenylethyl alcohol, rhodinol, cinnamon alcohol, cis-3-hexenol, menthol, α-terpineol, Sandela (3-isocamphyl- (5) -cyclohexanol), Aldehvde. such as citral, α-hexylcinnamaldehyde, hydroxy citronellal, LiUal® (p-tert-butyl-α-methyl-dihydrocinnamaldehyde), methylnonylacetaldehyde, phenylacetaldehyde, anisaldehyde, vanillin,
- Ketone. wie Allyljonon, α-Jonon, ß-Jonon, Isoraldein (Isomethyl- α-jonoή), Verbenone, Nootkaton, Geranylaceton,- ketones. such as allyl Jonon, α-Jonon, β-Jonon, Isoraldein (Isomethyl-α-jonoon), Verbenone, Nootkaton, Geranylacetone,
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.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.
Lactone. wie γ-Undecalacton, δ-Decalacton, Pentadecan-15-olid,Lactones. such as γ-undecalactone, δ-decalactone, pentadecan-15-olide,
verschiedene, in der Parfumerie oft benützte Komponenten, wie Indol, p-Menthan-8-thiol-3-on, Methyleugenol, Eugenol, Anethol, etc.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 Riechstofϊkompositionen, insbesondere solcher blumiger, blumig¬ würziger, blumig-fruchtiger und blumig-orientalischer Richtung, bestechen besonders durch ihre Originalität.The fragrance compositions produced using compounds I, in particular those with a floral, floral-spicy, floral-fruity and floral-oriental direction, are particularly impressive due to 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 (alkohoUsche 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 parfümiertenWhen used as a fragrance, the compound I can be used within wide limits, which can range, for example, from about 0.1 (detergents) to about 30 percent by weight (alcoholic solutions) in compositions without these values being intended to represent limit values, however the experienced perfumer can achieve effects with even lower concentrations or build new complexes with even higher doses. The preferred concentrations range between about 1 and about 20 percent by weight. The compositions prepared with the compounds I can be perfumed for all types
Verbrauchsgütern einsetzen (Eaux de Cologne, Eaux de Toilette, Extraits, Lotionen, Cremes, Shampoos, Seifen, Salben, Puder, Desodorantien, Detergentien, Gewebeveredler, Bleichmittel, Weichspüler für Textilien, usw. 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 WA. Poucher, Perfumes, Cosmetics and Soaps 2_, 7. Auflage, Chapman und Hall, London, 1974 hervorgeht.Use consumer goods (Eaux de Cologne, Eaux de Toilette, extras, lotions, creams, shampoos, soaps, ointments, powders, deodorants, detergents, fabric finishers, bleaches, fabric softeners, 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. In the production of such compositions, the above-mentioned known fragrances or mixtures of fragrances can be used in a manner known to (the perfumer), as can be seen, for example, from WA. Poucher, Perfumes, Cosmetics and Soaps 2_, 7th edition, Chapman and Hall, London, 1974.
Beispiel 1example 1
Chvpre KompositionChvpre composition
GewichtsteileParts by weight
B enzylsalicylat 100Benzyl salicylate 100
Ambrette-moschus 100Ambrette musk 100
Hydroxycitronellal 100Hydroxycitronellal 100
Sandela® Givaudan 100Sandela® Givaudan 100
Vetivenylacetat 50Vetivenylacetate 50
Patchouliöl 50Patchouli oil 50
Ylang-Ylang-öl 40Ylang-ylang oil 40
Methylnonylacetaldehyd 10% in Propylenglykol 40Methylnonylacetaldehyde 10% in propylene glycol 40
Galbanumöl 10% in Alkohol 40Galbanum oil 10% in alcohol 40
Melissenöl 30Melissa oil 30
Eichenmoos löslich 30Oak moss soluble 30
Styrallylacetat 30Styrallyl acetate 30
Zimtalkohol 20Cinnamon alcohol 20
Aldehyd C-ll (10-Undecenal) 10% in Propylenglykol 20Aldehyde C-ll (10-undecenal) 10% in propylene glycol 20
Vernaldehyd 20Vernaldehyde 20
Eugenol extra 20Eugenol extra 20
Majoranöl 10Marjoram oil 10
Weihrauch-resinoid 10 γ-Undecalakton 10% in Propylenglykol 10Frankincense resinoid 10 γ-undecalactone 10% in propylene glycol 10
Heliotropin 30Heliotropin 30
Rhodinol extra 5QRhodinol extra 5Q
900 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.900 If you add 100 parts I to this somewhat heavy chypre composition, it is changed very pleasantly fresh in the direction of 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 lighter, fresher; it is very suitable for men's colognes of a modern character.
Beispiel 2Example 2
Parfumerie-Komposition in Richtung HvacinthePerfume composition towards Hvacinthe
Gew ichtsteil«Part by weight «
Phenyläthylalkohol 200Phenylethyl alcohol 200
Hydroxy citronellal 100Hydroxy citronellal 100
Zimtalkohol 100Cinnamon alcohol 100
Phenyläthylisobutyrat 80Phenylethyl isobutyrate 80
Phenylpropylalkohol 60Phenylpropyl alcohol 60
Benzylaetat 50Benzyl acetate 50
Baccartol® Givaudan (Rosenbase auf Basis Citronelle-öl/ aceton-kondensationsprodukt 40Baccartol® Givaudan (rose base based on citronelle oil / acetone condensation product 40
Phenyläthylformiat 40Phenylethyl formate 40
Citronellol 30Citronellol 30
Eugenol 20Eugenol 20
Galbanum-öl 20Galbanum oil 20
Phenylacetaldehyd 10% in Propylenglykol 20Phenylacetaldehyde 10% in propylene glycol 20
Maltol 1% in Propylenglykol 20Maltol 1% in propylene glycol 20
Dimethylacetat des Hydratropaldehyds 10Dimethyl acetate of hydratropaldehyde 10
GeranylacetatGeranyl acetate
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. Beispiel 3If you add 200 parts I to this hyacinth base, it will soon appear much more typical of hyacinths. I advantageously combines with the components that make up the green note by making it appear much softer. Example 3
Parfumerie-Komposition in Richtung WeissdornPerfume composition towards hawthorn
GewichtsteileParts by weight
Terpineol 250 α-Hexylzimtaldehyd 100Terpineol 250 α-hexyl cinnamaldehyde 100
Phenyläthylalkohol 140Phenylethyl alcohol 140
Hydroxycitronellal 100Hydroxycitronellal 100
Anisaldehyd ex Anethol Θ0Anisaldehyde ex anethole Θ0
Heliotropin 50 Linalool 40Heliotropin 50 Linalool 40
Benzylacetat 30Benzyl acetate 30
Geraniol 30Geraniol 30
Bergamotte-öl 30 α-Jonon 20 Ambrette-moschus 20Bergamot oil 30 α-Jonon 20 Ambrette musk 20
Citronellol 10Citronellol 10
Aethylen-brassylat 10Ethylene brassylate 10
Methylacetophenon 10Methyl acetophenone 10
Coumarin 10 Indol pur 5Coumarin 10 pure indole 5
Geranylacetat 5Geranyl acetate 5
Phenylacetaldehyd 5Phenylacetaldehyde 5
Civette absolue 10% in Propylenglykol 5Civette absolute 10% in propylene glycol 5
Ylang-Ylang-öl 10 Isoeugenol 5Ylang-ylang oil 10 isoeugenol 5
Phenylacetaldehyd-dimethylacetal 5_Phenylacetaldehyde dimethylacetal 5_
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.If you add 50 parts of I to this floral-sweet composition, its powdery note is beautifully dressed in a floral-pink variant. A pleasantly gentle note emerges.
Ausserdem kommt eine Honig-note zur Geltung, welche der Base mehr Diffusion verleiht. — In addition, a honey note comes into play, which gives the base more diffusion. -
Beispiel 4Example 4
Parfumerie-Komposition in Richtung GardeniaPerfume composition towards Gardenia
GewichtsteileParts by weight
Hydroxy citronellal 120Hydroxy citronellal 120
Benzylacetat 100Benzyl acetate 100
Bergamotte-öl 100 α-Jonon 100Bergamot oil 100 α-Jonon 100
Neroli-öl 70Neroli oil 70
Styrallylacetat 70Styrallyl acetate 70
Linalool 70Linalool 70
Heliotropin 50Heliotropin 50
Ylang-Ylang-Öl 50Ylang-ylang oil 50
Keton-moschus (4-tert.Butyl-3,5-dinitro-2,6- dimethyl-acetophenon) 50Ketone Musk (4-tert-butyl-3,5-dinitro-2,6-dimethyl-acetophenone) 50
Isoeugenol 30Isoeugenol 30
Jasmin-öl 30 α-Hexylzimtaldehyd 30Jasmine oil 30 α-hexyl cinnamaldehyde 30
Ambrette-moschus 30Ambrette musk 30
Phenylacetaldehyd 50% in Propylenglykol 15Phenylacetaldehyde 50% in propylene glycol 15
Civette absolue 10% in Propylenglykol 5Civette absolute 10% in propylene glycol 5
Aldehyd C-10 (n-Decyl-) 10% in Propylenglykol 5Aldehyde C-10 (n-decyl) 10% in propylene glycol 5
Orangenöl kalifornisch fiCalifornian orange oil fi
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. If you add 70 parts I to this flowery base in the direction of Gardenia, it gets a strengthening honey note, which makes the base appear much more rounded. I makes the base look much more harmonious. I is a very balancing factor in the composition.

Claims

Patentansprüche claims
1. Cyclohexyliden-phenylacetonitril als Riechstoff.1. Cyclohexylidene-phenylacetonitrile as a fragrance.
2. Cyclohexyliden-phenylacetonitril als säure- und alkalistabiler Riechstoff.2. Cyclohexylidene-phenylacetonitrile as an acid and alkali-stable fragrance.
3. Cyclohexyliden-phenylacetonitril als Riechstoff für die3. Cyclohexylidene-phenylacetonitrile as a fragrance for the
Waschmittelindustrie.Detergent industry.
4. Cyclohexyliden-phenylacetonitril als Riechstoff für die Kosmetik.4. Cyclohexylidene-phenylacetonitrile as a fragrance for cosmetics.
5. Cyclohexyliden-phenylacetonitril als Riechstoff für Rosen- und/oder Geraniumnoten.5. Cyclohexylidene-phenylacetonitrile as a fragrance for rose and / or geranium notes.
6. Riechstoffkompositionen, gekennzeichnet durch einen Gehalt an Cyclohexyliden-phenylacetonitril.6. Fragrance compositions, characterized by a content of cyclohexylidene-phenylacetonitrile.
7. Säure- und alkalistabile Riechstoftkompositionen gemäss Anspruch 6.7. Acid and alkali-stable fragrance compositions according to claim 6.
8. Riechstoftkompositionen gemäss Anspruch 6 für die8. fragrance compositions according to claim 6 for the
Verwendung in der Kosmetikindustrie.Use in the cosmetics industry.
9. Riechstoftkompositionen gemäss Anspruch 6 für die Verwendung in der Waschmittelindustrie.9. fragrance compositions according to claim 6 for use in the detergent industry.
10. Riechstoftkompositionen gemäss Anspruch 6 mit Rosen- und/oder Geraniumnoten.10. fragrance compositions according to claim 6 with rose and / or geranium notes.
11. Verwendung von Cyclohexyliden-phenylacetonitril als Riechstoff.11. Use of cyclohexylidene-phenylacetonitrile as a fragrance.
12. Verwendung von Cyclohexyliden-phenylacetonitril als säure- und alkalistabiler Riechstoff.12. Use of cyclohexylidene-phenylacetonitrile as an acid- and alkali-stable fragrance.
13. Verwendung von Cyclohexyliden-phenylacetonitril als13. Use of cyclohexylidene-phenylacetonitrile as
Riechstoff für die Waschmittelindustrie.Fragrance for the detergent industry.
14. Verwendung von Cyclohexyliden-phenylacetonitril als Riechstoff für die Kosmetikindustrie. 14. Use of cyclohexylidene-phenylacetonitrile as a fragrance for the cosmetics industry.
15. Verwendung von Cyclohexyliden-phenylacetonitril als Riechstoff für Rosen- und/oder Geraniumnoten.15. Use of cyclohexylidene-phenylacetonitrile as a fragrance for rose 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
CH309395 1995-11-01
CH3093/95 1995-11-01
PCT/CH1996/000377 WO1997016512A1 (en) 1995-11-01 1996-10-24 Nitrile

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

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DE (1) DE59607690D1 (en)
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WO (1) WO1997016512A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP2086594A1 (en) * 2006-11-07 2009-08-12 Givaudan SA Malodor counteracting compositions
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
CN106795102B (en) * 2014-12-08 2019-09-20 弗门尼舍有限公司 Aliphatic nitrile with rose fragrant smell

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Publication number Priority date Publication date Assignee Title
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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Title
See references of WO9716512A1 *

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US6069125A (en) 2000-05-30
JP3802068B2 (en) 2006-07-26
EP0858498B1 (en) 2001-09-12
ES2162101T3 (en) 2001-12-16
JP2000514104A (en) 2000-10-24
DE59607690D1 (en) 2001-10-18
WO1997016512A1 (en) 1997-05-09

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