EP0191365A1 - Oximes araliphatiques, procédé pour leur préparation et compositions odoriférantes contenant de tels composés - Google Patents

Oximes araliphatiques, procédé pour leur préparation et compositions odoriférantes contenant de tels composés Download PDF

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Publication number
EP0191365A1
EP0191365A1 EP86101178A EP86101178A EP0191365A1 EP 0191365 A1 EP0191365 A1 EP 0191365A1 EP 86101178 A EP86101178 A EP 86101178A EP 86101178 A EP86101178 A EP 86101178A EP 0191365 A1 EP0191365 A1 EP 0191365A1
Authority
EP
European Patent Office
Prior art keywords
compounds
oil
methyl
trimethyl
oximes
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
EP86101178A
Other languages
German (de)
English (en)
Other versions
EP0191365B1 (fr
Inventor
Paul Albert Dr. Ochsner
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
L Givaudan and Co 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 L Givaudan and Co SA filed Critical L Givaudan and Co SA
Publication of EP0191365A1 publication Critical patent/EP0191365A1/fr
Application granted granted Critical
Publication of EP0191365B1 publication Critical patent/EP0191365B1/fr
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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • the invention relates to new fragrances. These are the compounds of the formula wherein R is hydrogen, methyl or ethyl.
  • Formula I is intended to encompass the syn and anti forms of oxime I.
  • the anti form is preferred.
  • the invention further relates to a process for the preparation of the compounds I.
  • This process is characterized in that a ketone of the formula where R has the above meaning, reacted with hydroxylamine or one of its salts.
  • the reaction of the compound of formula II with hydroxylamine or a salt thereof can be carried out according to methods known per se, see e.g. Organics, basic organic chemistry internship, author collective; 7th edition; VEB German Publishing House of Sciences; Berlin 1967, 375, 555:
  • the oxime is conveniently left as a salt, e.g. react as hydrochloride or sulfate in an alcoholic solution containing pyridine or sodium acetate or in an aqueous-alcoholic solution with the ketone II; the reaction temperature is preferably the reflux temperature of the reaction mixture.
  • the processing is expediently carried out according to methods known per se: distilling off most of the alcohol, adding an organic solvent, washing with water and finally removing the unreacted ketone.
  • the starting ketones II are known or can be prepared by methods known per se, e.g. by chain extension of the commercially available diisopropyl ketone, for example using arylalkyl halides.
  • the compounds I have special organoleptic properties which make them particularly suitable as fragrances.
  • the invention accordingly also relates to the use of the compounds I as fragrances.
  • the oximes according to the invention are distinguished by a special combination of perfume properties. They are either colorless or slightly colored, easily accessible, the individual approaches have a constant smell, are not irritating, stable and easy to use.
  • the compounds of formula I are reminiscent of notes of black currant. Sage. Grapes.
  • the compounds of the formula I can be used within wide limits, which can range, for example, from 0.01 (detergents) to 50% (alcoholic solutions) in compositions, without these values being intended to represent limit values, however, since the experienced perfumer can use even lower ones Concentrations can achieve effects or can build up new types of complexes with even higher doses. The preferred concentrations are moving between 0.05 and 10%.
  • the compositions produced with I can be used for all types of perfumed consumer goods (Eaux de Cologne, Eaux de Toilette, 1%s, lotions, creams, shampoos, soaps, ointments, powder, deodorants, detergents, tobacco, etc.).
  • the compounds I can accordingly be used in the production of compositions and - as the above compilation shows - using a wide range of known fragrances.
  • the known fragrances listed above can be used in a manner known to the perfumer, e.g. from W.A. Poucher, Perfumes, Cosmetics and Soaps 2, 7th edition, Chapman and Hall. London. Emerged in 1974.
  • the residue now consists of the crude oxime.
  • This crude oxime can e.g. in the form of a 10% or even a 1% solution in isopropyl myristate can be used in perfumery.
  • the 2,4,4-trimethyl-5-phenyl-3-heptanone can be obtained by alkylating diisopropyl ketone with 1-chloro-l-phenylpropane; Bp 78-79 ° C / 0.2 mmHg.
  • the resulting Cologne base appears much more natural.
  • the slightly campy note of bornylacetate that was noticed before is covered by the addition of the oxime.
  • Sandalore's sandal note is emphasized.
  • the new base also looks more diffusive. The effect achieved by adding the oxime corresponds to the effect that would be achieved by adding a natural product.

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)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP86101178A 1985-02-06 1986-01-30 Oximes araliphatiques, procédé pour leur préparation et compositions odoriférantes contenant de tels composés Expired EP0191365B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH52785 1985-02-06
CH527/85 1985-02-06

Publications (2)

Publication Number Publication Date
EP0191365A1 true EP0191365A1 (fr) 1986-08-20
EP0191365B1 EP0191365B1 (fr) 1989-08-02

Family

ID=4189045

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86101178A Expired EP0191365B1 (fr) 1985-02-06 1986-01-30 Oximes araliphatiques, procédé pour leur préparation et compositions odoriférantes contenant de tels composés

Country Status (4)

Country Link
US (1) US4654169A (fr)
EP (1) EP0191365B1 (fr)
JP (1) JPH0794421B2 (fr)
DE (1) DE3664766D1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019076926A1 (fr) * 2017-10-17 2019-04-25 S H Kelkar & Company Limited Substances odorantes et compositions comprenant des substances odorantes

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4827012A (en) * 1988-02-23 1989-05-02 Basf Corporation Oxo-ionol carbonates
US4992106A (en) * 1988-02-23 1991-02-12 Basf Corporation Novel oxo-ionol carbonates useful as tobacco flavorants
JP2001271092A (ja) 2000-03-27 2001-10-02 Takasago Internatl Corp 芳香性漂白剤組成物
US7494968B2 (en) * 2004-05-13 2009-02-24 Firmenich Sa Non-cyclic hindered ketones as perfuming ingredient
MXPA06013035A (es) 2004-05-13 2006-12-20 Firmenich & Cie Cetonas no ciclicas impedidas como ingrediente de perfumeria.
JP6248861B2 (ja) * 2014-08-19 2017-12-20 信越化学工業株式会社 化学増幅レジスト材料及びパターン形成方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4284814A (en) * 1978-09-08 1981-08-18 Hercules Incorporated Propene trimer and propene tetramer and use thereof in perfumery
EP0085352A2 (fr) * 1982-02-03 1983-08-10 L. GIVAUDAN & CIE Société Anonyme Oximes insaturées, leurs procédés de préparation et leur utilisation comme parfum et dans les compositions de parfum

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4052194A (en) * 1974-01-24 1977-10-04 Merrill Wilcox Oxime abscission agents
EP0045861B1 (fr) * 1980-08-08 1984-10-03 L. GIVAUDAN & CIE Société Anonyme Composés insaturés, leur procédé de préparation, leur utilisation comme parfums ainsi que les compositions parfumantes les contenant
JPS5913714A (ja) * 1982-07-13 1984-01-24 Taito Pfizer Kk 外用消炎鎮痛剤

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4284814A (en) * 1978-09-08 1981-08-18 Hercules Incorporated Propene trimer and propene tetramer and use thereof in perfumery
EP0085352A2 (fr) * 1982-02-03 1983-08-10 L. GIVAUDAN & CIE Société Anonyme Oximes insaturées, leurs procédés de préparation et leur utilisation comme parfum et dans les compositions de parfum

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019076926A1 (fr) * 2017-10-17 2019-04-25 S H Kelkar & Company Limited Substances odorantes et compositions comprenant des substances odorantes
US11549079B2 (en) 2017-10-17 2023-01-10 S H Kelkar & Company Limited Odorants and compositions comprising odorants

Also Published As

Publication number Publication date
JPH0794421B2 (ja) 1995-10-11
US4654169A (en) 1987-03-31
EP0191365B1 (fr) 1989-08-02
JPS61183261A (ja) 1986-08-15
DE3664766D1 (en) 1989-09-07

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