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
  • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms

Definitions

• the present invention relates to the use of a mixture of ice and trans-3-methyl- ⁇ -decalactone, such a mixture containing fragrance compositions and perfumed articles and a method for producing a fragrance composition.
• fragrances which have additional positive secondary properties in addition to their primary, namely olfactory properties, such as. B. a higher stability under certain conditions of use, a higher yield or better adhesion, or else lead to better sensory profiles through synergy effects with other fragrances.
• olfactory properties such as. B. a higher stability under certain conditions of use, a higher yield or better adhesion, or else lead to better sensory profiles through synergy effects with other fragrances.
• olfactory properties such as. B. a higher stability under certain conditions of use, a higher yield or better adhesion, or else lead to better sensory profiles through synergy effects with other fragrances.
• olfactory properties such as. B. a higher stability under certain conditions of use, a higher yield or better adhesion, or else lead to better sensory profiles through synergy effects with other fragrances.
• the quantities and number of fragrances in formulations can be minimized, which leads to sustainable conservation of resources when perfuming consumer and consumer goods.
• this primary object is achieved by using a mixture, which comprises ice and trans-3-methyl- ⁇ -decalactone in a molar ratio in the range from 2: 3.5 to 3.5: 2, as the jasmon fragrance.
• eis or trans-3-methyl- ⁇ -decalactone in each case encompasses the pure (ice or trans) enantiomers and their enantiomer mixtures, in particular the racemic mixtures.
• the invention is based on the surprising finding that a mixture of ice and trans-3-methyl- ⁇ -decalactone is suitable as a jasmine fragrance, although the individual substances are not jasmine fragrances.
• the structural formula of a mixture of ice and trans-3-methyl- ⁇ -decalactone is shown below:
• Chem. Express 1992, 7, 901 describes the photochemical synthesis of the racemic mixture of ice and trans-3-methyl- ⁇ -decalactone.
• Synlett 2001, 5, 629 describes the synthesis of cis, trans-3-methyl- ⁇ -decalactone on a solid phase system starting from a crotylstannane reagent and heptanal.
• JP-A2 2000-086647 describes an enantioselective synthesis for both enantiomers of cis-3-methyl- ⁇ -decalactone. Use in perfume oils and aromas is described.
• JP-A2 09-169624 relates to the use of Cn-C 16 - ⁇ -lactones as antimicrobial agents in toothpaste or mouthwash.
• the perfumers did not rate either the pure cis isomer with its coconut effects or the pure trans isomer with its fruity peach aspects as the most valuable product, but according to the table above, the mixtures of both isomers with a molar cis / trans ratio of 60:40 or 40:60 (i.e. 3: 2 or 2: 3). This applies both with regard to the olfactory evaluation, as well as for application-technical criteria such as the adhesion to smell strips and the charisma.
• the optimal mixing ratio of the isomers is around a cis content of 36.4 - 63.6% and a corresponding trans content of 63.6 - 36.4%.
• Another aspect of the present invention relates to the use of cis- 3-methyl- ⁇ -decalactone in a fragrance composition containing trans-3-methyl- ⁇ -decalactone, for enhancing the peach mediated by trans-3-methyl- ⁇ -decalactone -Geruchs.
• the addition of cis-3-methyl- ⁇ -decalactone can increase the peach smell of trans-3-methyl- ⁇ -decalactone, even though the cis compound itself has no such peach smell; the cis connection acts as an enhancer. It follows from the foregoing that a jasmine-like smell aspect is added at the same time, which cannot be determined either with the pure ice or with the pure trans compound.
• the invention also relates to a method for imparting, enhancing or modifying a jasmine odor in a fragrance composition, the fragrance composition comprising an amount of a mixture of ice and trans-3-methyl- ⁇ -decalactone in a molar ratio in the range of 2: 3, 5 to 3.5: 2 is added, which is sufficient to impart, enhance or modify a jasmine smell.
• a fragrance composition is initially assumed which does not initially have a jasmine odor
• this fragrance composition can be provided with a jasmine odor by adding said mixture of ice and trans-3-methyl- ⁇ -decalactone.
• an amount of the mixture must be used which is sufficient to impart the jasmine odor within the fragrance composition that is created.
• the mixture can be added Ice and trans-3-methyl- ⁇ -decalactone can be used to enhance or modify the smell of jasmon.
• the invention further relates to a method for producing a fragrance composition with a strong peach smell and a jasmine smell, with the following steps: providing a fragrance base composition that has no strong peach smell, mixing the fragrance base composition with the compounds fertilize cis-3-methyl- ⁇ -decalactone and trans-3-methyl- ⁇ -decalactone, with the proviso that (i) these compounds in a molar cis trans ratio in the range from 2: 3.5 to 3.5: 2 are used, (ii) the total amount of the compounds used is sufficient to impart the strong peach smell and the jasmine smell and (iii) the amount of trans-3-methyl- ⁇ -decalactone used in the absence of cis-3-methyl - ⁇ -decalactone is not sufficient to impart the strong peach smell.
• a fragrance composition with a strong peach smell is produced by adding a compound (trans-3-methyl- ⁇ -decalactone) which itself only is able to give off a faint peach smell and additionally a compound (cis-3-methyl- ⁇ -decalactone) is added as an enhancer, which is suitable for the one given by trans-3-methyl- ⁇ -decalactone Enhance peach smell.
• the invention also relates to a method for enhancing a peach smell mediated by trans-3-methyl- ⁇ -decalactone in a fragrance composition, an effective amount of cis-3-methyl- ⁇ -decalactone being added to the fragrance composition.
• the present invention also relates to a fragrance composition or a scented article with a jasmine odor, comprising a quantity of a mixture of ice and trans-3 which brings about the jasmine smell.
• Methyl- ⁇ -decalactone in a molar cis / trans ratio in the range from 2: 3.5 to 3.5: 2 with neither the cis-3-methyl- ⁇ -decalactone used alone nor the trans-3 used -Methyl- ⁇ -decalactone by itself causes the Jasmine smell.
• Such a fragrance composition or such a perfumed article also has a strong peach smell.
• the amount of the mixture of ice and trans-3-methyl- ⁇ -decalactone used is preferably in the range from 0.01 to 99.9% by weight, preferably 0.1 up to 90% by weight and particularly preferably 0.5 to 70% by weight, based on the total weight of the perfume oil composition.
• the olfactory properties, material properties (such as solubility in common cosmetic solvents, compatibility with the usual other constituents of such products, etc.) and the toxicological harmlessness of the mixtures to be used according to the invention underline their particular suitability for the purposes mentioned.
• Fragrance compositions according to the invention or perfumed articles which contain an amount of a mixture of ice and trans-3-methyl- ⁇ -decalactone which is not only sufficient to give a jasmine odor are particularly preferred mediate, but also to convey, modify and / or enhance a peach-like or coconut-like scent.
• fragrance compositions in the production of fragrance compositions according to the invention, jasmonic or peach, coconut and lactone-like odor notes can be used in many variations.
• the example below of a perfume fragrance theme (“Jenny”) clearly demonstrates the olfactory effect of a mixture of cis / trans-3-methyl- ⁇ -decalactone.
• a perfume oil of the "Jenny” type can be characterized as floral, modern and transparent , The base perfume oil already contains the trans-3-methyl- ⁇ -decalactone; by adding cis-3-methyl- ⁇ -decalactone, the fruity (peach-like) notes are surprisingly clearly enhanced and the fragrance composition also gets a jasmine-like aspect.
• a mixture of cis / trans-3-methyl- ⁇ -decalactone (with a molar ratio in the range 2: 3.5 to 3.5: 2) is particularly suitable for use in perfume compositions because of its olfactory properties.
• the cis trans mixture can be combined with a large number of other fragrances and used in numerous products.
• the combination with other odoriferous substances in different quantitative ratios can be combined particularly advantageously to form novel perfume compositions.
• a fragrance composition with a peach, coconut and lactone note can be produced, for example, by mixing the mixture of ice and trans-3-methyl- ⁇ -decalactone with constituents of a base fragrance composition, the mixture of ice and trans 3-methyl- ⁇ -decalactone is used in an amount sufficient to modify and / or enhance the smell of the base fragrance composition.
• fragrances with which the mixture to be used according to the invention can advantageously be combined can be found, for example, in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, Adverlag or K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Material, 4 rd . Ed., Wiley-VCH, Weinheim 2001.
• Extracts from natural raw materials such as essential oils, concretes, absolues, resins, resinoids, balms, tinctures such as B.
• fragrances from the group of hydrocarbons such as 3 - cooking; pinene; beta-pinene; ⁇ -terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; Famesen; limonene; longifolene; myrcene; ocimene; Valencene; (E, Z) -1,3,5-undecatriene; styrene; diphenylmethane;
• aliphatic alcohols such as e.g. hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) - and (Z) -3-hexenol-1-octen-3-ol; Mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-nonadienol; 3,7-dimethyl-7-methoxyoctane-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
• aliphatic aldehydes and their acetals such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2-methyl nonanal; (E) -2-hexenal; (Z) -4-heptenal; 2,6-dimethyl-5-heptenal; 10- undecenal; (E) -4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10-trimethyl-5,9-undecadienal; Heptanaldiethylacetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; 1 - (1-methoxypropoxy) - (E / Z) -3- hexene; aliphatic ketones and their oximes such as 2-heptanone;
• aliphatic nitriles such as e.g. 2-nonenoic acid nitrile; 2-Undecen Textrenitril; 2-tridecenonitrile; 3,12-Tridecadien Aciditril; 3,7-dimethyl-2,6-octadienonitrile; 3,7-dimethyl-6-octen Aciditril;
• ester of aliphatic carboxylic acids such as e.g. (E) - and (Z) -3- hexenyl formate; ethylacetoacetate; isoamyl; hexyl acetate; 3,5,5
• Butyl butyrate ; isoamyl; hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate;
• acyclic terpene alcohols such as B. Citronellol; geraniol; nerol; linalool; lavandulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-
• cyclic terpene alcohols such as B. menthol; isopulegol; alpha-terpineol; Terpinenol-4; Menthane-8-ol; Menthane-1-ol; Menthane-7-ol; borneol; Isobomeol; linalool; monopoly; cedrol; ambrinol; Vetyverol; guaiol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoate;
• cyclic alcohols such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-lsocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5 J E9-cyclododecatrien-1 -ol; 2-isobutyl-4-methyl tetrahydro-2H-pyran-4-ol;
• cycloaliphatic alcohols such as e.g. alpha, 3, 3-
• cyclic and cycloaliphatic ethers such as e.g. cineol; Cedryl methyl ether; cyclododecyl; 1, 1 -dimethoxycyclododecane; (Ethoxymethoxy) cyclododecane; alpha-Cedrenepoxid; 3a, 6,6,9a-
• cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcycIopentanon; 2
• heptylcyclopentanone 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert.-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1 J 2,3,3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone; cyclohexadecanone;
• cycloaliphatic aldehydes such as 2,4-dimethyl ⁇ 3-cyclohexenecarbaldehyde; 2-methyl-4- (2 I 2,6-trimethyl-cyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexenecarbaldehyde;
• cycloaliphatic ketones such as. B. 1 - (3,3-Dimethylcyclohexyl) -4-penten-1-one; 2,2-dimethyl-1- (2,4-dimethyl-3-cyclohexen-1-yl) -1-propanone; 1- (5,5- Dimethyl-1-cyclohexen-1-yl) -4-penten-1-one; 2,3,8,8-tetramethyl-1, 2,3,4,5,6,7,8-octahydro-2-naphthalenyl methyl ketone; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienyl ketone; tert-butyl- (2 I 4-dimethyl-3-cyclohexen-1-yl) ketone;
• esters of cyclic alcohols such as e.g. 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-
• ester of cycloaliphatic alcohols such as 1-cyclohexylethyl crotonate ;
• ester of cycloaliphatic carboxylic acids such as. B. allyl 3-cyclohexyl propioate; Allylcyclohexyloxyacetat; ice and trans methyl dihydrojasmonate; ice and trans methyl jasmonate; Methyl 2-hexyl-3-oxocyclopentane carboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; Ethyl 2-methyl-1,3-dioxolane-2-acetate;
• araliphatic alcohols such as benzyl alcohol; 1-PhenylethylaIkohol; 2-phenylethyl alcohol; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phenylethyl alcohol; 1, 1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl; 1 - (4-isopropylphenyl) ethanol; the ester of araliphatic alcohols and aliphatic carboxylic acids such as benzyl acetate; benzylpropionate; benzyl isobutyrate
• the araliphatic ether such as e.g. 2-phenylethyl; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether; Phenylacetaldehyde dimethylacetal; Phenylaeetaldehyddiethylaeetal; Hydratropaaldehyde dimethyl acetal; Phenylacetaldehydglycerinacetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydroindeno [1,2-d] -m-dioxin; 4,4a, 5,9b-tetrahydro-2,4-dimethylindeno [1,2-d] -m-dioxin;
• aromatic and araliphatic aldehydes such as.
• aromatic and araliphatic ketones such as acetophenone; 4-methyl acetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthalenyl) ethanone; 2-benzofuranylethanone; (3-methyl-2-benzofuranyl) ethanone; benzophenone; 1,1,2,3,3,6-hexamethyl-5- indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanylmethyl ketone; 1 - [2,3-dihydro-1, 1, 2,6-tetramethyl-3- (1-methylethyl) -1 H-5-indenyl] ethanone; 5 ', 6', 7 ', 8'-tetrahydro-S'.S'. ⁇ '. ⁇ '. ⁇ ' ⁇
• aromatic and araliphatic carboxylic acids and their esters such as e.g. benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate; Hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; Geranylphenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethylcinnamat; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl; Hexylsalieylat; cyclohexyl; Cis-3-hexenyl salicylate; Benzyl salicylate; phenylethyl; Methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenylgly
• nitrogenous aromatic compounds such as e.g. 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.-butylacetophenone;
• phenols, phenyl ethers and phenyl esters such as, for example, estragole; anethole; Eugenei; Eugenylmethylether; isoeugenol; Isoeugenylmethylether; thymol; Carvaerol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-naphthyl isobutyl ether; 1,4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; p-Kresylphenylacetat; the heterocyclic compounds such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4
• the lactones such as 1,4-octanolide; 3-methyl-1,4-octanoIid; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide, 4-methyl-1,4-decanolide; 1.15 pentadecanolide; ice and trans-11-pentadecen-1,15-olide; ice and trans-12-pentadecen-1,15-olide; 1,16-hexadecanolide; 9-hexadecene-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa- 1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide; Ethylene-1,12-dodecanedioate; Ethylene-1,
• the perfume oils containing the lactone mixture to be used according to the invention can be used in liquid form, undiluted or diluted with a solvent for perfuming.
• 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 lactone mixture to be used according to the invention can be adsorbed on a carrier which ensures both a fine distribution of the fragrances in the product and a controlled release during use.
• a carrier which ensures both a fine distribution of the fragrances in the product and a controlled release during use.
• Such carriers can be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, gas concrete etc. or organic materials such as woods and cellulose-based substances.
• the perfume oils containing the lactone mixture to be used according to the invention can also be microencapsulated, spray-dried, present as inclusion complexes or as extrusion products and added in this form to the product to be perfumed. If necessary, the properties of the perfume oils modified in this way can be further optimized by so-called “coating” with suitable materials with a view to a more targeted fragrance release, for which purpose wax-like plastics such as polyvinyl alcohol are preferably used.
• the microencapsulation of the perfume oils can, for example, by the so-called coacervation process with the aid of capsule materials e.g. made of polyurethane-like substances or soft gelatin.
• the spray-dried perfume oils can be produced, for example, by spray drying an emulsion or dispersion containing the perfume oil, it being possible to use modified starches, proteins, dextrin and vegetable gums as carriers.
• 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 obtained by fusing the perfume oils with a suitable wax-like substance and by extrusion with subsequent solidification, if necessary in a suitable solvent, e.g. Isopropanol.
• the perfume oils containing the lactone mixture to be used according to the invention can be used in concentrated form, in solutions or in the modified form described above for the production of, for example, perfume extracts, eau de perfumes, eau de toilettes, aftershaves, eau de colognes, pre-shave Products, splash colognes and scented refreshing wipes as well as the scenting of acidic, alkaline and neutral cleaning agents, such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam-like carpet cleaners, liquid Detergents, powder detergents, laundry pretreatment agents such as bleaching agents, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants and air fresheners applied in liquid, gel-like or on a solid carrier shape, aerosol sprays, waxes and polishes such as furniture polishes, floor wax, shoe creams and body care products such as solid and liquid soaps,
• the total amount of the lactone mixture to be used according to the invention is 0.01 to 99.9% by weight, preferably 0.1 to 90% and particularly preferably 0.5 to 70%, based on the total fragrance composition.
• the base perfume oil of the "Jenny” type is enhanced by the addition of cis-3-methyl- ⁇ -decalactone (instead of the ineffective solvent DPG) flowery, hedionic and jasmon-like; the fruity (peach-like) aspects are enhanced.
• Ice and trans-3-methyl- ⁇ -decalactone are prepared in a known manner according to the process design from the following reference: Izvestiya Akadii Nauk SSSR, Seriya Khimieheskaya, 1971, 2, 389.

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  • 2004-06-19 DE DE102004029809A patent/DE102004029809A1/de not_active Withdrawn
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