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
  • C11B9/0007—Aliphatic compounds
  • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom

Definitions

• the invention relates to perfume compositions containing 4,8-dimethyl-3,7-nonadien-2-one included and their use.
• fragrances Despite a large number of existing fragrances, the perfume industry does further need for new fragrances, beyond their olfactory properties have additional positive secondary properties, e.g. higher stability, higher yield, better adhesion to textiles and higher stability.
• Perfume compositions were found that have E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one of the formulas contained as a single isomer or as a mixture.
• the compound of the invention is generally a mixture of two isomers in front.
• E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one is new in perfume compositions. It is surprising that E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one not only the known ones in fragrance compositions has olfactory properties, but is strengthened in the composition and so can be perceived even in the smallest quantities.
• compositions are more stable in color than compositions with comparable odor properties.
• E and / or Z-4,8-Dimethyl-3,7-nonadien-2-one instead of other similar fragrances, such as Citronellal or Citral, there are no discolourations in the perfume composition. Color changes in the perfume composition lead to a smaller one Acceptance. It is therefore a goal of the perfume industry to maintain the color stability of perfume compositions to increase.
• 4,8-Dimethyl-3,7-nonadien-2-one also has the surprising property, the fragrance impression to be permanently fixed, visibly refreshed and rounded off.
• E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one is suitable excellent for use in perfume compositions.
• E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one according to the invention can usually be found in small doses in the resulting perfume compositions radiantly fresh, rounded scents achieve, the overall smell strikingly harmonizing, the cosmetic-floral effective radiation is perceptibly increased and the fixation, i.e. the Adhesion of the perfume oil is significantly strengthened.
• fragrances which can be combined according to the invention with E- and / or Z-4,8-dimethyl-3,7-nonadien-2-one to give perfume compositions can be found, for example, in S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair , NJ, 1969, self-published or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 3 rd . Ed ., Wiley-VCH , Weinheim 1997.
• Extracts from natural raw materials such as essential oils, concretes, absolute, resins, resinoids, balms, tinctures such as B. Ambratincture; Amyris oil; Angelica seed oil; Angelica root oil; Anise oil; Valerian oil; Basil oil; Baummoos -Absolue; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; Birch tar oil; Bitter almond oil; Savory oil; Bucco leaf oil; Cabreuva oil; Cade oil; Calmus oil; Camphor oil; Cananga oil; Cardamom oil; Cascarilla oil; Cassia oil; Cassie absolute; Castoreum-absolue; Cedar leaf oil; Cedarwood oil; Cistus oil; Citronell oil; Lemon oil; Copaiva balm; Copaiva balsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts absolute;
• the perfume oils containing the compounds according to the invention can be found in liquid form, undiluted or diluted with a solvent for Perfumes are used.
• Suitable solvents for this are e.g. Ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, Isopropyl myristate etc.
• the perfume oils containing the compounds according to the invention can be adsorbed on a carrier, which is both for a fine distribution of the Fragrances in the product as well as for a controlled release during use worries.
• a carrier which is both for a fine distribution of the Fragrances in the product as well as for a controlled release during use worries.
• Such supports can be porous inorganic materials such as light sulfate, Silica gels, zeolites, gypsum, clays, clay granules, gas concrete etc. or organic Materials like woods and cellulose-based fabrics.
• perfume oils containing the compounds according to the invention can also microencapsulated, spray dried, as inclusion complexes or as extrusion products are available and added in this form to the product to be perfumed become.
• the properties of the perfume oils modified in this way can be changed So-called "coating" with suitable materials with a view to a more targeted fragrance release be further optimized, which is why wax-like plastics such as e.g. Polyvinyl alcohol can be used.
• the microencapsulation of the perfume oils can, for example, by the so-called coacervation process with the help of capsule materials e.g. made of polyurethane-like Fabrics or soft gelatin.
• the spray-dried perfume oils can for example by spray drying an emulsion containing the perfume oil, or dispersion are prepared, modified starches as carriers, Proteins, dextrin and vegetable gums can be used.
• Inclusion complexes can e.g. by adding dispersions of the perfume oil and Cyclodextrins or urea derivatives in a suitable solvent, e.g. Water.
• Extrusion products can be made by fusing the Perfume oils with a suitable waxy substance and by extrusion with subsequent solidification, if necessary in a suitable solvent, e.g. Isopropanol, be preserved.
• the amount used is that of the invention Compounds 0.05 to 50 wt .-%, preferably 0.5 to 20%, based on the entire composition.
• the perfume compositions according to the invention can be in concentrated form, in Solutions or in modified form described above can be used for the Manufacture of fine perfumery products and industrial products.
• Fine perfumery products and industrial products are e.g. Perfume Extraits, Eau de Perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave products, Splash colognes and scented refreshing towels as well as scented acidic, alkaline or neutral cleaning agents, e.g.
• Skin creams and lotions face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, After-shave creams and lotions, tanning creams and lotions, hair care products such as.
• hair styling agents such as Cold waves and hair straighteners, hair lotions, hair creams and lotions, deodorants and antiperspirants such as Armpit sprays, roll-ons, deosticks, deocremes
• Decorative cosmetics products such as Eye shadows, nail polishes, Make-ups, lipsticks, mascara and candles, lamp oils, incense sticks, Insecticides, repellents, fuels.
• the amount of perfume composition 0.1 to 40 wt .-%, preferably 0.5 to 20 wt .-%, based on the Final product.
• 4,8-Dimethyl-3,7-nonadien-2-one can advantageously be obtained from 4,8-dimethyl-3,7-nonadien-2-ol be manufactured, e.g. by a Grignard reaction of citral and methyl magnesium chloride was synthesized (Indian Perfum., 1983, 27, 112-18).
• the Oxidation to 4,8-dimethyl-3,7-nonadien-2-one is known (e.g. C. Aguilar et al. Bol.
• An advantageous process for the preparation of 4,8-dimethyl-3,7-nonadien-2-one is characterized in that 4,8-dimethyl-3,7-nonadien-2-ol in the presence of a
• Catalyst and a hydrogen acceptor is implemented.
• This reaction dispenses with critical reagents and is also problem-free larger scale feasible.
• Aluminum alkoxides such as aluminum tri-tertiary butylate and Aluminum triisopropylate, preferably aluminum triisopropylate can be used.
• the reaction temperature is between 40 ° C and reflux temperature, preferably between 60-120 ° C.
• the known compounds can be used as the hydrogen acceptor (Org. Reactions, Vol. 6, pp.207-272).

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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)
• Cosmetics (AREA)
• Detergent Compositions (AREA)

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Publications (2)

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• 1999
  • 1999-12-21 DE DE19961598A patent/DE19961598A1/de not_active Withdrawn
• 2000
  • 2000-12-08 EP EP00126525A patent/EP1111029A3/fr not_active Withdrawn
  • 2000-12-11 JP JP2000375778A patent/JP2001181670A/ja active Pending
  • 2000-12-13 US US09/736,599 patent/US20010005711A1/en not_active Abandoned

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