EP0200890B1 - Verwendung von einem Spirolacton als Riechstoff - Google Patents

Verwendung von einem Spirolacton als Riechstoff Download PDF

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Publication number
EP0200890B1
EP0200890B1 EP86103491A EP86103491A EP0200890B1 EP 0200890 B1 EP0200890 B1 EP 0200890B1 EP 86103491 A EP86103491 A EP 86103491A EP 86103491 A EP86103491 A EP 86103491A EP 0200890 B1 EP0200890 B1 EP 0200890B1
Authority
EP
European Patent Office
Prior art keywords
oxaspiro
decan
composition
perfuming
lactone
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
Application number
EP86103491A
Other languages
English (en)
French (fr)
Other versions
EP0200890A1 (de
Inventor
François Dr. Delay
Wolfgang Klaus Giersch
Günther Dr. Ohloff
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 EP0200890A1 publication Critical patent/EP0200890A1/de
Application granted granted Critical
Publication of EP0200890B1 publication Critical patent/EP0200890B1/de
Expired 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
    • 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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0088—Spiro compounds
    • 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
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/44—Perfumes; Colouring materials; Brightening agents ; Bleaching agents
    • C11D9/442—Perfumes

Definitions

  • the present invention relates to the field of perfumery. It relates in particular to the use of a spirannic lactone of formula (I) or 1-oxaspiro [4.5] decan-2-one, as a perfuming agent.
  • the subject of the invention is also a perfuming composition characterized in that it contains, as active perfuming agent, said spirannic lactone.
  • As preferred compounds are 8-isopropyl-1-oxaspiro [4.5] decan-2-one and 8-ethyl-1-oxaspiro [4.5] decan-2-one.
  • 1-oxaspiro [4.5] decan-2-one also has interesting odorous properties and that, therefore, it could be used as an active perfuming ingredient for the preparation of perfumes and perfuming bases and for the perfuming of various articles such as soaps, detergents, solid and liquid, ionic, anionic, zwitterionic or non-ionic, textile softeners, cleaning products or cosmetics, shampoos and body deodorants.
  • the lactone of the invention Used as active adjuvant in polymeric bases or various resins, can serve as active principle for deodorizing or sanitizing devices for ambient air or closed chambers.
  • 1-oxaspiro [4.5] decan-2-one can be described as hot, spicy, lactonic in the direction of rose or tuberose and coumarin.
  • 8-methyl-1-oxaspiro [4.5] decan-2-one described in the European application cited above, it can be noted that the latter compound has a less elegant, more lactonic, type note. coconut with a distinctly oily shade.
  • 1- oxaspiro [4.5] decan-2-one develops a floral-type lactonic note.
  • 1-oxaspiro [4.5] decan-2-one can be used at higher concentrations than the corresponding methylated counterpart.
  • the proportions in which the compound of the invention can develop the desired odorous characteristics can of course vary within a very wide range of values. Those skilled in the art know from experience that such values depend on the particular effect sought as well as on the nature of the products which it is desired to flavor. We also know that these values are a function of the nature of the other constituents in a given composition when spiro-lactone (I) is used as an ingredient in a perfuming base or in a concentrate mixed with other co-ingredients, common solvents or adjuvants.
  • proportions of the order of 5, 10 or even 20% by weight relative to the weight of the composition in which it is incorporated can be used without the smell of the resulting composition loses balance.
  • the spiro-lactone (I) can be used in accordance with the invention either by direct addition to the products which it is desired to flavor in the isolated state, or more generally in conjunction diaper with other fragrance ingredients, additives or carriers which are widely used in perfumery.
  • the perfume co-ingredients with which the compound of the invention can be combined in such use belong to various chemical classes, for example aldehydes, esters, ethers and alcohols; they can be natural or synthetic.
  • spiro-lactone (I) is a known compound which can be obtained using one of the methods described in the literature, for example by radical addition of an acrylic ester to cyclohexanol in the presence of an organic peroxide. Such a reaction is illustrated by diagram A.
  • di-tert-butyl peroxide has been indicated as organic peroxide, but of course other organic peroxides may also be suitable for promoting such a radical reaction which, in itself, is well documented in the prior art.
  • the spiro lactone (I) of the invention has the advantage of being prepared from readily available products, cyclohexanol and methyl acrylate , which increases its commercial interest.
  • a basic composition of the "Fern” type was prepared by mixing the following ingredients (parts by weight):
  • a basic composition of "Tuberose” type was prepared by mixing the following ingredients (parts by weight):
  • compositions containing 1-oxaspiro [4.5] decan-2-one had a warm and soft, tuberose-like note, while the composition containing 8-methyl-1-oxaspiro [4.5] decan-2-one developed a sweet-floral note of lactonic type without, however, showing the desired tuberous character.
  • the soap composition thus obtained had a flowery odor.
  • a solid detergent base was prepared by mixing the following ingredients (parts by weight):

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)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Claims (5)

1. Verwendung von 1-Oxaspiro[4.5]decan-2-on als Riechstoff in Parfümkompositionen und parfümierten Produkten.
2. Parfümkomposition, die eine Verbindung gemäß Anspruch 1 enthält.
3. Ein ionisches, anionisches, nicht-ionisches oder zwitterionisches Reinigungsmittel, das eine Verbindung gemäß Anspruch 1 enthält.
4. Ein Raumbedüfter, das eine Verbindung gemäß Anspruch 1 enthält.
5. Eine Seife, die eine Verbindung gemäß Anspruch 1 enthält.
EP86103491A 1985-04-19 1986-03-14 Verwendung von einem Spirolacton als Riechstoff Expired EP0200890B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1692/85 1985-04-19
CH169285 1985-04-19

Publications (2)

Publication Number Publication Date
EP0200890A1 EP0200890A1 (de) 1986-11-12
EP0200890B1 true EP0200890B1 (de) 1989-08-02

Family

ID=4216374

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86103491A Expired EP0200890B1 (de) 1985-04-19 1986-03-14 Verwendung von einem Spirolacton als Riechstoff

Country Status (4)

Country Link
US (1) US5057239A (de)
EP (1) EP0200890B1 (de)
JP (1) JPH0726112B2 (de)
DE (1) DE3664784D1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3930962A1 (de) * 1989-09-15 1991-03-28 Dragoco Gerberding Co Gmbh Verwendung von 1-oxaspiro(4.5)nonan-2-on als riechstoff
AU2002337422A1 (en) 2001-10-05 2003-04-22 Koninklijke Philips Electronics N.V. Compressed storage of data items
JP4608499B2 (ja) * 2003-11-04 2011-01-12 フイルメニツヒ ソシエテ アノニム 清涼調製物のための香気成分

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2839538A (en) * 1953-08-26 1958-06-17 Rohm & Haas Substituted butyrolactones
US2960441A (en) * 1957-09-17 1960-11-15 Warner Lambert Pharmaceutical Therapeutic compositions of salts of 3, 3-pentamethylene-4-hydroxybutyric acid
US3007940A (en) * 1960-03-01 1961-11-07 Warner Lambert Pharmaceutical Method of preparing derivatives of 3, 3-pentamethylene-4-hydroxybutyric acid
JPS5938236B2 (ja) * 1976-08-10 1984-09-14 宇部興産株式会社 γ，γ−ウンデカメチレンブチロラクトンの製法
CH626533A5 (de) * 1978-01-20 1981-11-30 Firmenich & Cie
DE3362298D1 (en) * 1982-08-12 1986-04-03 Firmenich & Cie Spirolactones, their use as perfumes, perfume compositions containing them and process for their preparation
JPS5959682A (ja) * 1982-08-25 1984-04-05 エル・ジボ−ダン・エ・コンパニ−・ソシエテ・アノニム スピロラクトン化合物およびその製造法
US4519944A (en) * 1982-08-25 1985-05-28 Givaudan Corporation Spirolactones as odorants
DE3306798A1 (de) * 1983-02-26 1984-08-30 Henkel KGaA, 4000 Düsseldorf Neue oxaspirododecan-derivate, deren herstellung und verwendung als riechstoffe sowie diese enthaltende riechstoffkompositionen

Also Published As

Publication number Publication date
JPS61246116A (ja) 1986-11-01
DE3664784D1 (en) 1989-09-07
US5057239A (en) 1991-10-15
JPH0726112B2 (ja) 1995-03-22
EP0200890A1 (de) 1986-11-12

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