EP1078028B1 - Utilisation d'aldehydes monocycliques comme matieres odorantes - Google Patents

Utilisation d'aldehydes monocycliques comme matieres odorantes Download PDF

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Publication number
EP1078028B1
EP1078028B1 EP99920865A EP99920865A EP1078028B1 EP 1078028 B1 EP1078028 B1 EP 1078028B1 EP 99920865 A EP99920865 A EP 99920865A EP 99920865 A EP99920865 A EP 99920865A EP 1078028 B1 EP1078028 B1 EP 1078028B1
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EP
European Patent Office
Prior art keywords
hydroformylation
aldehydes
methyl
monocyclic
fragrance
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
EP99920865A
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German (de)
English (en)
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EP1078028A1 (fr
Inventor
Thomas Markert
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Kao Corp SA
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Kao Corp
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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
    • C11B9/0003—Compounds of unspecified constitution defined by the chemical reaction for their preparation
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms

Definitions

  • the invention relates to the use of specific monocyclic aldehydes which are obtainable by partial or complete hydroformylation of (di) methyl-substituted cyclooct (adi) s as fragrances.
  • (di) methyl-substituted is meant that the bicyclic system carries either one or two methyl groups as substituents.
  • the invention relates to the use of monocyclic aldehydes, which are obtainable by partial or complete hydroformylation of (Di) methyl-substituted Cyclooct (adi) enes, as fragrances.
  • Another object of the invention is the use of monocyclic Aldehydes obtainable by partial or complete hydroformylation of (di) methyl-substituted Cyclooct (adi) enes, as a fragrance booster.
  • monocyclic Aldehydes obtainable by partial or complete hydroformylation of (di) methyl-substituted Cyclooct (adi) enes, as a fragrance booster.
  • 3a), (3b) described in more detail below and (3c) particularly preferred.
  • the preparation of the aldehydes to be used according to the invention is advantageously carried out by hydroformylation of (di) methyl-substituted cyclooct (adi) s.
  • the latter compounds have as common backbone on a cyclooctane system.
  • hydroformylation is known to one skilled in the art Reaction that was discovered in 1938 by von Roelen. These are alkenes converted into aldehydes with carbon monoxide and hydrogen. The reaction is too known as oxo synthesis.
  • methyl-substituted Cyclooctadienes can be used in hydroformylation be carried out partially or completely. In the partial Hydroformylation remains an olefinic double bond per molecule of Starting compound while only the other hydroformylieil, at In complete hydroformylation, two CHO groups are incorporated into the molecule introduced. If, however, as starting materials (di) methyl-substituted cyclooctenes Of course, only the complete one is used Hydroformylation possible because only one olefinic double bond per molecule the starting compound is present.
  • the odor profile of the hydroformylation products of the invention is original and novel.
  • perfume compositions they enhance harmony and harmony Radiation as well as the adhesion, whereby the dosage under Consideration of the remaining components of the composition on each desired scent is matched.
  • the hydroformylation products according to the invention are suitable because of their Odor profiles especially for modifying and amplifying known Compositions. Emphasized in particular is their extraordinary Odor strength, which generally contributes to the refinement of compositions.
  • the compounds (3a), (3b) and (3c) - compare the structural formulas below - for the inventive use as a fragrance and / or fragrance booster. Accordingly, the use of the compounds (3a), (3b) and (3c), for example, in Griffinbeduftern particularly advantageous. In addition, it has been found that the compounds (3a), (3b) and (3c) can be used with particular advantages in cleaning agents for strengthening citrus diets.
  • the compounds (3a), (3b) and (3c) can be, for example, by Hydroformylation of the corresponding (di) methyl-substituted cyclooctene or produce cyclooctadiene systems.
  • the usable proportions of the hydroformylation products according to the invention in Fragrance compositions range from 0.001 to 70 wt .-%, based on the entire mix.
  • the hydroformylation products according to the invention and Compositions of this kind can be used both for perfuming cosmetic Preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, Toothpastes, mouthwashes, deodorants as well as in extract perfumery be used.
  • perfuming cosmetic Preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, Toothpastes, mouthwashes, deodorants as well as in extract perfumery be used.
  • perfuming technical products as well as detergents and cleaners, fabric softeners, Textile treatment or tobacco.

Landscapes

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

Claims (6)

  1. Utilisation d'aldéhydes monocycliques que l'on peut obtenir par hydroformylation partielle ou complète de cyclooct(adi)ènes à substitution diméthyle comme produits odorants.
  2. Utilisation des aldéhydes monocycliques de formule développée ci-dessous
    Figure 00150001
    comme produits odorants.
  3. Utilisation d'aldéhydes monocycliques que l'on peut obtenir par hydroformylation partielle ou complète de cyclooct(adi)ènes à substitution diméthyle comme renforçateurs de parfum.
  4. Utilisation des aldéhydes monocycliques de formules développées ci-dessous
    Figure 00150002
    comme renforçateurs de parfum.
  5. Utilisation d'aldéhydes monocycliques que l'on peut obtenir par hydroformylation partielle ou complète de cyclooct(adi)ènes à substitution diméthyle, dans des préparations cosmétiques, des produits industriels ou en parfumerie alcoolique.
  6. Utilisation des aldéhydes monocycliques de formules développées ci-dessous
    Figure 00160001
    dans des préparations cosmétiques, des produits industriels ou en parfumerie alcoolique.
EP99920865A 1998-04-17 1999-04-08 Utilisation d'aldehydes monocycliques comme matieres odorantes Expired - Lifetime EP1078028B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19817043A DE19817043A1 (de) 1998-04-17 1998-04-17 Verwendung von monocyclischen Aldehyden als Riechstoffe
DE19817043 1998-04-17
PCT/EP1999/003207 WO1999054430A1 (fr) 1998-04-17 1999-04-08 Utilisation d'aldehydes monocycliques comme matieres odorantes

Publications (2)

Publication Number Publication Date
EP1078028A1 EP1078028A1 (fr) 2001-02-28
EP1078028B1 true EP1078028B1 (fr) 2005-08-03

Family

ID=7864830

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99920865A Expired - Lifetime EP1078028B1 (fr) 1998-04-17 1999-04-08 Utilisation d'aldehydes monocycliques comme matieres odorantes

Country Status (7)

Country Link
US (1) US6541446B1 (fr)
EP (1) EP1078028B1 (fr)
JP (1) JP2002512301A (fr)
DE (2) DE19817043A1 (fr)
ES (1) ES2246569T3 (fr)
IL (1) IL139026A0 (fr)
WO (1) WO1999054430A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6271193B1 (en) 2000-10-11 2001-08-07 International Flavors & Fragrances Inc. Carbon containing functional group substituted 4,5,6,7-tetrahydro-polyalkylated-4-indanes, isomers thereof, processes for preparing same and uses thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3985769A (en) 1974-11-15 1976-10-12 Universal Oil Products Company Acetal derivatives of cyclooctyl carboxaldehydes
US3984478A (en) * 1975-05-27 1976-10-05 Universal Oil Products Company Hydroformylation process
DE2849742B2 (de) 1978-11-16 1980-10-16 Henkel Kgaa, 4000 Duesseldorf Verfahren zur Herstellung von Aldehyden und Verwendung der Verfahrensprodukte als Riechstoffe
US4306085A (en) * 1979-07-05 1981-12-15 Shell Oil Company Hydroformylation process using resin-ligand-metal catalyst
JPS5821638A (ja) 1981-07-31 1983-02-08 Mitsubishi Petrochem Co Ltd ジアルデヒド類の製造方法

Also Published As

Publication number Publication date
IL139026A0 (en) 2001-11-25
DE19817043A1 (de) 1999-10-21
US6541446B1 (en) 2003-04-01
JP2002512301A (ja) 2002-04-23
DE59912360D1 (de) 2005-09-08
EP1078028A1 (fr) 2001-02-28
ES2246569T3 (es) 2006-02-16
WO1999054430A1 (fr) 1999-10-28

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