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
  • C11B9/0026—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 present invention relates- to the use of unsaturated ketones of a specific structure as fragrances.
• fragrances due to their demand, are available in completely insufficient quantities. For example, 5,000 kg of rose petals are needed to produce 1 kg of rose oil. The consequences include a greatly limited annual production worldwide and a high price. It is therefore apparent that the fragrance industry has a constant need for new fragrances that exhibit interesting scents. On the one hand, the range of naturally available fragrances can be supplemented thereby, on the other hand it is thus possible to make the necessary adaptations to the ever-changing fashion in taste. Furthermore, this makes it possible to meet the ever-increasing demand for scent enhancers for products of daily use, such as cosmetics and cleaning agents.
• the subject matter of the present invention is, initially, the use of unsaturated ketones of general structure (I) where the groups R 1 , R 2 , R 3 , R 4 and R 5 independently represent H or 1 to 6 C alkyl groups, which can be saturated or unsaturated, straight-chained, branched or cyclic, for use as fragrances.
• compounds (I) and, in particular, compounds (I-a), (I-b) and (I-c) can be employed individually or blended together.
• a particularly preferred use is that of (I-a).
• blends of compounds (I) are used.
• the invention relates to fragrance concentrates comprising one or more of the compounds of general structure (I) described above in detail.
• Compounds (I) according to the invention are characterized by an odour characteristic in which fruity and herbal qualities dominate. They have excellent stability in formulations for cosmetics and perfumes of daily use.
• Compounds (I) may be produced, per se, on the basis of synthesizing techniques known in organic chemistry. Particularly suitable possibilities for the production of compounds (I) can be gathered from the section dealing with the examples.
• a further subject matter of the invention is a method of producing compounds of the aforementioned general formula (I).
• 1-acetyl-4-methyl-cyclo-3-hexene or 1-(1,1-diethoxyethyl)-4-methylcyclohex-3-ene is reacted with olefinically unsaturated alkenols, the OH group of the alkenols being in alpha position relative to the C ⁇ C double bond of the alkenol.
• the OH group of the alcohols is preferably primary, but may also be secondary or tertiary.
• compounds (I) enhance harmony and emanation as well as naturalness and staying power. Dosage is tailored to whichever scent is being striven for, while taking the composition's other constituents into account.
• formula (I) compounds are, furthermore, particularly suitable for modifying and enhancing known compositions. Particular emphasis should be placed on their outstanding intensity of scent, which contributes, in a quite general way, toward the composition's refinement.
• Formula (I) compounds can be combined using numerous known fragrance ingredients, such as other perfumes of a natural, synthetic or partially synthetic origin, essential oils and plant extracts.
• the range of natural fragrances may include components that are both readily volatile as well as ones that exhibit medium and low volatility.
• the range of synthetic fragrances may include representatives of virtually any substance class.
• compositions range from approximately 1-70% by weight, based on the entire mixture.
• Blends of compounds (I) according to the invention as well as compositions of this type can be used both to perfume cosmetic preparations, such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, toothpastes, mouthwash and deodorants, as well as in alcoholic perfumery (e.g. eau de cologne, eau de toilette, extracts).
• perfume cosmetic preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, toothpastes, mouthwash and deodorants
• alcoholic perfumery e.g. eau de cologne, eau de toilette, extracts
• perfume technical products such as detergents and cleaning agents, fabric softeners and textile treating agents.
• compositions are added thereto in an amount effective olfactorily, in particular in a concentration of 0.01 to 2% by weight, based on the entire product.
• the mixture produced in this way was transferred to a steel autoclave insert and heated to 190° C. for 5 hours under 20 bar nitrogen.
• the GC control showed that the educt had been reduced down to 2% and that 31.5% main product had formed.
• reaction mixture- washed neutral in a separating funnel, the organic phase was separated and dried over sodium sulphate.
• Low-boiling components were removed by distillation in a water jet vacuum until about 80° C.
• the residue of about 190 g was distilled in a 30-cm Vigreux column.
• the main quantity of 80 g (boiling point 50-60° C./0.2 mbar) with a GC purity of 80% was once more distilled in a Vigreux column, with 50 g of product with a purity of 95.3% being obtained.
• the 1 H-NMR spectrum (400 MHz in CDCl 3 ) showed 1 methyl group (2 singlets) at 1.6 ppm and was overlapped by 1 CH 2 group (doublets, atom adjacent to the olefinic C atom in the cyclohexene ring on which the methyl group is located). 3 further CH 2 groups (2 in the cyclohexene ring and adjacent to the double bond in the side chain) showed two multiplet signals at 1.95 (intensity 4H) and 2.1 ppm (intensity 2H).
• Scent characteristic when first smelled, Davana, fruity, green, Muguet and after 24 hours on the scent strip, the subsequent smell was faintly redolent of rhubarb.
• the proton adjacent to the keto group and located on the cyclohexene ring appeared as a strongly split up multiplet at 2.2 ppm.
• the olefinc protons showed a ddd at 5.9 ppm (1H), a doublet of the doublet at 5.0 ppm (2Hs) and a broad signal for the olefinic proton in the cyclohexene ring at 5.4 ppm.
• Scent characteristic when first smelled, it was green, fruity, lardaceous, lime, and after 24 hours on the scent strip, the scent was redolent of fruit, wood, Muguet, bergamot.
• the methyl group at the end of the side chains produced a signal peak of overlapped triplets at 0.9 ppm (3Hs).
• Two multiplets (approx. 4Hs) were located between 1.1. and 1.4 ppm, probably they are to be assigned to the 2 CH 2 groups from the side chain.
• the methyl group on the cyclohexene ring produced broad singlets at 1.6 and 1.7 ppm (approx. 1.5 Hs each).
• Two further signal clusters (approx. 3Hs) corresponding to a CH group and a CH 2 group that were adjacent to the keto group in beta position and to a double bond were found at 1.9 and 2.0 ppm.
• Two singlets each with one echo (approx.
• Scent characteristic when first smelled, it was green, herbal, fresh, citrus, jasmone quality; after 24 hours on the scent strip, the subsequent smell was redolent of terpene, grapefruit, peel.

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• 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)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Cosmetics (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

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• 2002
  • 2002-03-19 DE DE10212026A patent/DE10212026A1/de not_active Ceased
• 2003
  • 2003-02-17 US US10/507,203 patent/US20050119158A1/en not_active Abandoned
  • 2003-02-17 EP EP03744331.4A patent/EP1485350B1/fr not_active Expired - Lifetime
  • 2003-02-17 WO PCT/EP2003/001561 patent/WO2003078391A1/fr active Application Filing
  • 2003-02-17 ES ES03744331T patent/ES2426001T3/es not_active Expired - Lifetime
  • 2003-02-17 JP JP2003576397A patent/JP4346448B2/ja not_active Expired - Fee Related
• 2008
  • 2008-11-03 US US12/263,603 patent/US7582600B2/en not_active Expired - Fee Related

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