EP0504563B1 - Geruchsstoff mit einer Spiranstruktur - Google Patents

Geruchsstoff mit einer Spiranstruktur Download PDF

Info

Publication number
EP0504563B1
EP0504563B1 EP92101748A EP92101748A EP0504563B1 EP 0504563 B1 EP0504563 B1 EP 0504563B1 EP 92101748 A EP92101748 A EP 92101748A EP 92101748 A EP92101748 A EP 92101748A EP 0504563 B1 EP0504563 B1 EP 0504563B1
Authority
EP
European Patent Office
Prior art keywords
spiro
perfuming
ene
tridec
ingredient
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.)
Expired - Lifetime
Application number
EP92101748A
Other languages
English (en)
French (fr)
Other versions
EP0504563A1 (de
Inventor
Wolfgang Klaus Giersch
Pierre-Alain Blanc
Karl-Heinrich Schulte-Elte
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Firmenich SA
Original Assignee
Firmenich SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firmenich SA filed Critical Firmenich SA
Publication of EP0504563A1 publication Critical patent/EP0504563A1/de
Application granted granted Critical
Publication of EP0504563B1 publication Critical patent/EP0504563B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • 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
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms

Definitions

  • the present invention relates to the field of perfumery. It relates more particularly to the use of a spiranic ketone compound of formula or spiro [5.7] tridéc-1-ene-3-one, as a perfuming ingredient for the preparation of perfumes and perfumed products.
  • Spiro [5.7] tridec-1-ene-3-one is a known chemical entity. Kane Vinayak described its preparation from enamines of cycloaliphatic aldehydes by reaction with methyl vinyl ketone [Synth. Common. 6 , 237-42 (1976)].
  • a similar synthesis has been proposed by NR Natale et al. [Org. Prep. Proced. Int.
  • triconvergec-1-ene-3-one is used to develop iridescent notes recalling by some of its aspects 5-ethyl-2-nonanol or p-tert-amylcyclohexanone [Orivone: IFF; see S. Arctander, Perfume and Flavor Chemicals, sec. 166, Montclair, N.J. USA (1969)].
  • the spiro-ketone of the invention also has a costus, animal and leather appearance, its base notes recalling flax and coumarin. With excellent olfactory power, spiro-ketone (I) has very good substantivity on linen, particularly on cotton fabrics.
  • spiro-ketone (I) The proportions in which spiro-ketone (I) is used to develop the desired odorous effects can vary within a fairly wide range of values. Given its power, concentrations of the order of 0.5-1% may, in many cases, be sufficient. Lower concentration values can be used when perfuming functional or maintenance products, for example in soaps or detergents, where concentrations of 0.1% can already promote the desired effects. Of course, these concentration values should not be interpreted restrictively, those skilled in the art know from experience that in any practical use, the determination of such values depends on the nature of the products which it is desired to flavor as well as that of the co-ingredients in a given composition.
  • triconvergec-1-ene-3-one can be used in an isolated state, but more generally it will be used in admixture with usual diluents, carriers or excipients, as well as with other perfuming ingredients currents. Many examples of such co-ingredients and additives are provided in the prior art [see for example S. Arctander, op. cit.].
  • the present invention therefore relates, in addition to the use as defined above, a perfuming composition and products fragrances containing spiro [5.7] tridec-1-ene-3-one as an active fragrance ingredient.
  • spiro [5.7] tridec-1-ene-3-one is a known compound which can be obtained by following one of the preparation methods described in the cited documents, for example from cyclooctanecarboxaldehyde by reaction with methyl vinyl ketone in the presence of p-toluenesulfonic acid.
  • the product obtained was identical in all respects to the indications provided by the literature.
  • a basic perfuming composition for powdered detergents was prepared by mixing the following ingredients: Ingredients Parts by weight Benzyl acetate 250 Phenylethyl acetate 100 Styrallyl acetate 125 Aldehyde C9 10% * 50 Aldehyde C10 10% * 50 Allyl amyl glycolate 50 Methyl anthranilate 10% * 50 Citronellol 50 Verdyl acetate 25 Diphenyloxide 10% * 200 P-tert-butylcyclohexyl acetate 250 Clove essence from Madagascar 100 Galaxolide 50 MIP 1) 200 Galione 2) 50 Raw Geraniol (Glidden) 465 100 Lilial ® 3) 100 Linalol 1000 Purified menthone 10% * 250 Essence of patchouli 125 Phenylethyl phenylacetate 50 Brazilian orange essence 125 Amyl salicylate 100 Benzyl salicylate 150 Hexyl salicylate 3500 Terpineol ord.
  • a basic perfume composition of the vetyver type was prepared by mixing the following ingredients: Ingredients Parts by weight Essence of vetyver Haiti 500 Rhubofix 1) 20 Vertofix heart 2) 260 Cedroxide 3) 100 Cedrol 100 Total 980 1) epoxyethyl-methyltricycloundecene; origin: Firmenich SA, Geneva, Switzerland 2) origin: International Flavors and Fragrances Inc., USA 3) epoxy trimethylcyclododecatriene; origin: Firmenich SA, Geneva, Switzerland The addition, at a rate of 2% of spiro [5.7] tridéc-1-ene-3-one to the perfume base thus prepared reinforces the woody-vetyver aspect of the composition while giving it a natural character.

Landscapes

  • 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)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Claims (5)

  1. Verwendung des Spiro[5,7]tridec-1-en-3-ons als Riechstoffbestandteil.
  2. Riechstoffkomposition, dadurch gekennzeichnet, daß sie als aktiven Riechstoffbestandteil das Spiro[5,7]tridec-1-en-3-on zusammen mit üblichen Verdünnungsmitteln, Trägern oder Zusätzen sowie mit anderen üblichen Riechstoffzusätzen enthält.
  3. Parfümiertes Produkt, dadurch gekennzeichnet, daß es als aktiven Riechstoffbestandteil das Spiro[5,7]tridec-1-en-3-on enthält.
  4. Als parfümiertes Produkt gemäß Patentanspruch 3, eine Seife, ein Reinigungsmittel, ein Textilweichmacher, ein kosmetisches Mittel, eine Creme, ein Shampoo, ein Haarbehandlungsmittel, ein Pflegeprodukt oder ein Raumluftverbesserer.
  5. Ein Verfahren zur Verleihung, Verbesserung oder Veränderung der Dufteigenschaften einer Riechstoffkomposition oder eines parfümierten Verbrauchsgegenstandes, dadurch gekennzeichnet, daß man zu einer Parfümbase oder einem Verbrauchsgegenstand das Spiro[5,7]tridec-1-en-3-on in einem olfaktorisch wirksamen Anteil hinzufügt.
EP92101748A 1991-03-15 1992-02-03 Geruchsstoff mit einer Spiranstruktur Expired - Lifetime EP0504563B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH796/91 1991-03-15
CH79691 1991-03-15

Publications (2)

Publication Number Publication Date
EP0504563A1 EP0504563A1 (de) 1992-09-23
EP0504563B1 true EP0504563B1 (de) 1994-12-28

Family

ID=4195390

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92101748A Expired - Lifetime EP0504563B1 (de) 1991-03-15 1992-02-03 Geruchsstoff mit einer Spiranstruktur

Country Status (4)

Country Link
US (1) US5151410A (de)
EP (1) EP0504563B1 (de)
JP (1) JPH0570792A (de)
DE (1) DE69200982T2 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100337692C (zh) * 2005-03-16 2007-09-19 周娉 中药香水及其制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4261866A (en) * 1979-11-02 1981-04-14 Fritzsche Dodge & Olcott Inc. Spirodienones and spirocyclic ketones
NL8104271A (nl) * 1981-09-16 1983-04-18 Naarden International Nv Parfumcomposities en geparfumeerde produkten die spiroundecanonen en -undecenonen als parfumgrondstof bevatten.

Also Published As

Publication number Publication date
DE69200982D1 (de) 1995-02-09
EP0504563A1 (de) 1992-09-23
DE69200982T2 (de) 1995-05-11
US5151410A (en) 1992-09-29
JPH0570792A (ja) 1993-03-23

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