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WO2004002930A1 - Nouvelles substances odorantes et procede de fabrication - Google Patents

Nouvelles substances odorantes et procede de fabrication Download PDF

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Publication number
WO2004002930A1
WO2004002930A1 PCT/EP2003/006878 EP0306878W WO2004002930A1 WO 2004002930 A1 WO2004002930 A1 WO 2004002930A1 EP 0306878 W EP0306878 W EP 0306878W WO 2004002930 A1 WO2004002930 A1 WO 2004002930A1
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Prior art keywords
oil
methyl
mixture
compounds
dimethyl
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PCT/EP2003/006878
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German (de)
English (en)
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WO2004002930A8 (fr
Inventor
Erich Dilk
Peter Meyer
Karl-Heinz Bork
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Symrise AG
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Symrise AG
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Priority to AU2003246631A priority Critical patent/AU2003246631A1/en
Publication of WO2004002930A1 publication Critical patent/WO2004002930A1/fr
Publication of WO2004002930A8 publication Critical patent/WO2004002930A8/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/13—Monohydroxylic alcohols containing saturated rings
    • C07C31/133—Monohydroxylic alcohols containing saturated rings monocyclic
    • 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
    • C11B9/0038—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing more than six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C5/00—Candles
    • C11C5/002—Ingredients

Definitions

  • the invention relates to cyclododecylbutan-2-ols, their use as fragrances and as antimicrobial agents, a process for their preparation and products containing these compounds.
  • Fragrance substances with a cyclododecyl or cyclododecenyl structure are known. These often belong to the classes of acetals, esters, ketones or alcohols, with the specific odor notes of the compounds depending on the structure.
  • EP-A 0278384 is for the racemate of 2-Cyclododecylpropan-l-ol (Hydroxyambran ®) a flowery, warm, heavy wood odor and called a ambriert woody odor note for the corresponding ethyl ether.
  • Hydroxyambran ® 2-Cyclododecylpropan-l-ol
  • the (+) - 2-cyclododecylpropan-l-ol is described as almost odorless and the (-) - 2-cyclododecylpropan-1-ol as strongly amber-woody with a dominant amber character.
  • the invention relates inter alia to the use of 3-cyclododecylbutan-2-ols (formula A) and 1-cyclododecylbutan-2-ols (formula B) as fragrances.
  • the invention also relates to the compounds corresponding to formulas A and B, processes for their preparation and perfumed products and fragrance mixtures containing the compounds according to the invention.
  • the compounds according to the invention have complex wood-amber fragrance properties, surprisingly soft cedar-woody notes being dominant in these compounds. In addition, they have typical amber notes. In addition, the connections are characterized by long-lasting adhesion.
  • the compounds of the invention can advantageously be prepared by reacting cyclododecene with butan-2-one in step (a), preferably in the presence of a radical initiator, and then in step (b) the ketones formed in step (a) (Addition products) can be reduced, e.g. by reductive treatment of the reaction mixture containing the ketones.
  • step a In the reaction of cyclododecene with butan-2-one (step a), the molar
  • Ratio of butan-2-one to cyclododecene in general between 400 and 1, preferably between 150 and 1 and in particular between 50 and 5.
  • the radicals necessary for the reaction (step a) are generated by generally customary methods, with thermally induced decomposition of the added radical initiators being preferred.
  • Azo compounds e.g. 2,2'-
  • Azobis-isobutyronitrile and peroxide compounds can be used, the use of peroxides, in particular di-tert-butyl peroxide, being preferred.
  • the temperature range for carrying out the radical reaction (step a) is variable over a wide range. It is generally between 30 and 250 ° C, preferably 80 to 220 ° C. If di-tert-butyl peroxide is used as the radical initiator, work is preferably carried out at 120-200 ° C.
  • reaction (step a) is preferably under pressure, advantageously in one
  • Autoclaves carried out although very high pressures are possible. Is preferably carried out at a pressure between 2 and 20 bar.
  • the reaction mixture usually obtained after distillative removal of excess butan-2-one, possibly unreacted cyclododecene and low boilers formed contains, as addition products, both the 3-cyclododecyl and 1-cyclododecylbutan-2-ones and the corresponding ⁇ , ⁇ 8-unsaturated ones ketones.
  • the subsequent conversion of the reaction mixture obtained into the compounds according to the invention can be carried out in various ways.
  • route I the ⁇ , / 3-unsaturated ketones contained in the reaction mixture are first converted into the saturated ketones by hydrogenation of the olefinic double bond.
  • Hydride by subsequent reduction of the keto group with hydrides, such as sodium borohydride, Limiumalumim 'or lithium borohydride, the
  • reaction mixture obtained in the radical reaction is converted into the end products by simultaneous hydrogenation of the olefinic double bond and the carbonyl group in one reaction step.
  • Heterogeneous catalysts are generally used as hydrogenation catalysts, but suitable homogeneous catalysts can also be used.
  • suitable homogeneous catalysts can also be used.
  • Examples of hydrogenation catalysts, support materials and hydrogenation conditions are e.g. in Houben-Weyl, Methods of Organic Chemistry, Volume IV / lc, Vl / lb and VLT / 2c.
  • Palladium catalysts such as palladium on activated carbon can be used to hydrogenate the olefinic double bonds in accordance with route I.
  • Ruthenium catalysts such as ruthenium on activated carbon, can be used for the simultaneous hydrogenation of the olefinic double bond and the carbonyl group according to route II.
  • the hydrogenation (route I or H) is advantageously carried out at temperatures between 40 and 300 ° C, preferably between 50 and 150 ° C.
  • Hydrogen pressure is usually between 5 and 50 bar, preferably between 10 and 25 bar.
  • the compounds according to the invention are generally obtained as a mixture of the compounds corresponding to the formulas A and B.
  • the 3-cyclododecylbutan-2-ols are presumably present as a mixture of the syn and anti compounds (isomers 1 and 2).
  • the syn and anti nomenclature here refers to the stereoisomerism of the methyl and the hydroxyl group to one another.
  • the compounds according to the invention can therefore be used both as individual substances and as a mixture in a large number of products; They can be combined particularly advantageously with other fragrances in different, different proportions to form novel perfume compositions.
  • the use of the compounds according to the invention intensifies the radiance of perfume compositions and gives the composition freshness and liveliness.
  • the compounds according to the invention also bring about more volume in the odor and a softer and more rounded odor flow.
  • the compounds of the formulas A and B also have antimicrobial properties, in particular against gram-positive bacteria. Because gram-positive germs in cosmetics, oral hygiene and
  • deodorants such as armpit sprays, roll-ons, deo sticks, deodorant creams, gels or powders.
  • the compounds according to the invention are used in cosmetics and household products, they are notable for high stability.
  • the stability in antiperspirant products based on aluminum and zirconium salts, such as, for example, aluminum hydroxychloride, is particularly noteworthy, so that the compounds according to the invention are also outstandingly suitable for use in antiperspirants.
  • the invention therefore also relates to preparations, in particular cosmetic, dermatological and oral hygiene preparations, comprising an antimicrobially effective amount of a compound of the formula A or B or a mixture of
  • fragrances with which the butanols according to the invention can advantageously be combined can be found e.g. in S. Arctander, Perfume and Flavor Chemicals, Vol. I and II, Montclair, N.J., 1969, Edverlag or K. Bauer, D.
  • Extracts from natural raw materials such as essential oils, concretes, absolute,
  • Resins, resinoids, balms, tinctures such as B.
  • ambergris tincture Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil;
  • Basil oil Basil oil; Tree moss absolute; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; birch tar; Bitter almond oil; Savory oil; Buccorightöl;
  • Cabreuvaöl cade oil; calamus; camphor oil; Cananga oil; cardamom; Cascarilla oil; cassia; Cassie absolute; Beaver-absolue; Cedernseeöl; cedarwood;
  • Oil Oil; eucalyptus oil; Fennel oil; Pine needle oil; galbanum; Galbanumresin; geranium; Grapefruit oil; guaiac wood; gurjun balsam; gurjun balsam oil; Helichrysum absolute; Hehchrysumöl; Ginger oil; Iris root absolute; Orris root oil; Jasmine absolute; Kahnusöl; Chamomile oil blue; Roman chamomile oil; Carrot seed oil; Kaskarillaöl; Pine needle oil; spearmint; Seed oil; labdanum; Labdanum absolute; Labdanumresin; Lavandin absolute; lavender oil; Lavender absolute;
  • Lavender oil Lemongrass oil; Lovage oil; Distilled lime oil; Lime oil pressed; linaloe; Litsea cubeba oil; Bay leaf oil; Macisöl; Marjoram oil; Mandarin oil; Massoirindenöl; Mimosa absolute; Musk seed oil; musk tincture; Muscatel Sage Oil; nutmeg; Myrrh absolute; Myrrh oil; myrtle; Clove leaf oil; Clove flower oil; neroli; Olibanum absolute; olibanum; Opopanaxöl; Orange blossom absolute; Orange oil; oregano; Palmarosa oil; patchouli oil; perilla oil;
  • Pepper oil chilli; pine oil; Poleyöl; Rose absolute; Rosewood oil; Rose oil rosemary oil; Dalmatian sage oil; Sage oil spanish; sandalwood; Celery seed oil; spike lavender oil; star anise; Styraxöl; tagetes; Pine needle oil; Tea-tree oil;
  • hydrocarbons such as B. 3-carene; ⁇ -pinene; beta-pinene; ⁇ -terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -l, 3,5-undecatriene; styrene;
  • aliphatic alcohols such as hexanol; octanol; 3-octanol; 2,6-dimethyl-heptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) - and (Z) -3- hexenol; l-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-methoxyoctan-2-ol; 9-decenol; 10 -Undecenol; 4-methyl-3-decen-5-ol;
  • aliphatic aldehydes and their acetals such as e.g. 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-5,9-undecadienal; Heptanal diethyl acetal; 1, 1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde;
  • aliphatic ketones and their oximes such as e.g. 2-heptanone; 2-octanone; 3
  • octanone 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;
  • the aliphatic sulfur-containing compounds such. B .; 3-methylthiohexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercapto-hexyl butyrate; 3-acetylthiohexyl acetate; l-menthene-8-thiol;
  • aliphatic nitriles such as e.g. 2-nonenoic acid nitrile; 2-Tridecenklad; 2,12-tridecadienonitrile; 3, 7-dimethyl-2,6-octadienonitrile; 3, 7-dimethyl-6-octenoitrile;
  • aliphatic carboxylic acids and their esters such as e.g. (E) - and (Z) -3-hexenyl formate; ethylacetoacetate; isoamyl; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenyl acetate; Octyl acetate; 3-octyl acetate; l-octen-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl;
  • Citronellol Citronellol; geraniol; nerol; linalool; Lavadulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyl octane-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5, 7-octadien-2-ol; 2,6-dimethyl-3 5-octadien-2-ol; 3, 7-dimethyl-4,6-octadien-3-ol; 3,7-dimethyl-l, 5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octatrien-l-ol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pen
  • acyclic terpene aldehydes and ketones such as B .; geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl
  • cyclic terpene alcohols such as B. menthol; isopulegol; alpha-terpineol; Terpinenol-4; Menthane-8-ol; Menthane-1-ol; Menthane-7-ol; borneol; soborneol;
  • cyclic terpene aldehydes and ketones such as e.g. menthone; menthone; 8th-
  • Mercaptomenthan-3-one carvone; camphor; fenchon; alpha-ionone; beta-ionone; alpha-n-methyl ionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-Rron; alpha-damascone; beta-damascone; beta-damascenone; delta-damascone; gamma-damascone; 1 - (2,4,4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one; 1, 3,4,6,7,8a-hexahydro-1, 1,5,5-tetramethyl-2H-2,4a-methanonaphthalene-8 (5H) -one;
  • nootkatone Dihydronootkaton; alpha-sinensal; beta-sinensal; Acetylated cedarwood oil (methyl cedryl ketone);
  • cyclic alcohols such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecatrien-l-ol; 2-isobutyl-4-methyl tetrahydro-2H-pyran-4-ol; cycloaliphatic alcohols such as alpha, 3,3-trimethylcyclohexylmethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-l-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-l-yl) pentan-2-ol; 3-methyl-5
  • cyclic and cycloaliphatic ethers such as e.g. cineol; cedryl methyl ether; Cyclododecyl methyl ether; (Ethoxymethoxy) cyclododecane; alpha-Cedrenepoxid;
  • cyclic and macrocychic ketones such as 4-tert.-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 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-l-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (l-ethoxy-vinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert.-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1, 1, 2,3, 3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1
  • cycloaliphatic aldehydes such as 2,4-dimethyl-3-cyclohexenecarbaldehyde; 2-methyl-4- (2,2,6-trimethyl-cyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexenecarbaldehyde; 4- (4-methyl-3-penten-l-yl) -3-cyclohexenecarbaldehyde; the cycloaliphatic ketones such as. B.
  • esters of cyclic alcohols such as e.g. 2-tert-butylcyclohexyl acetate; 4-tert-butyl cyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; Deca- hydro-2-naphthylacetate; 3-Pentyltet ⁇ ahydro-2H-pyran-4-yl acetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthylacetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or 6-indenyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or 6-indenylpropionate;
  • ester of cycloahphatic carboxylic acids such as. B. allyl-3-cyclohexylpropionate; Allylcyclohexyloxyacetat; ice and trans methyl dihydrojasmonate; ice and trans
  • araliphatic alcohols such as e.g. benzyl alcohol; 1-phenylethyl; 2
  • phenylethyl 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-l-ol; 4-methoxybenzyl; l- (4-isopropylphenyl) ethanol;
  • esters of araliphatic alcohols and aliphatic carboxylic acids such as e.g.
  • the araliphatic ether such as e.g. 2-phenylethyl; 2-phenylethyl isoamyl ether; 2-Phenylethyl-l-ethoxyethyl ether; phenylacetaldehyde; Phenyl acetaldehyde diethylacetal; Hydratropaaldehyddimethylacetal; Phenylacetaldehyde glycerol acetal; 2,4,6-trimethyl-4-phenyl-l, 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 e.g. benzaldehyde; Phenylacetal dehyde; 3-phenylpropanal; Hydratropaaldehyd; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethyl ⁇ ro ⁇ anal; 2-methyl-3- (4-isopropylphenyl) propanal; 2-Methyl-3- (4-tert-butylphenyl) propanal; 3 - (4-tert-butylphenyl) propanal; cinnamic aldehyde; alpha-Butylzimtaldehyd; alpha-amyl cinnamic aldehyde; alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4
  • 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; benzophenone; 1, 1, 2,3,3, 6-hexamethyl-5-indanylmethyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone; l- [2,3-dihydro-l, l, 2,6-tetramethyl-3- (l-methylethyl) - lH-5-indenyl] ethanone; 5 ', 6' 5 7 ', 8'-tetrahydro-3', 5 ', 5', 6 ', 8', 8'-hexamethyl-2-aceto-naphthone;
  • 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; geranyl phenylacetate;
  • the nitrogenous aromatic compounds such as e.g. 2,4,6-trinitro-l, 3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.-butylacetophenone; Cinnamic acid nitrile; 5-phenyl-3-methyl-2-penten Aciditril; 5-phenyl-3-methylpentanoic acid nitrile; methyl anthranilate; Methyl N-methylanthranilate; See bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6-Isopropyl; 6-isobutylquinoline; 6-sec-butylquinoline; indole; skatol; 2-methoxy-3-iso ⁇ ropyl ⁇ yrazin; 2-isobutyl
  • phenols phenyl ethers and phenyl esters
  • phenyl esters such as e.g. estragole; anethole; eugenol;
  • heterocychic compounds such as e.g. 2,5-dimethyl-4-hydroxy-2H-furan-3-one;
  • lactones such as 1,4-octanolide; 3-methyl-l, 4-octanolide; 1,4-nonanolide; 1,4-
  • the perfume oils containing the compounds according to the invention can be used in liquid form, undiluted or diluted with a solvent for perfuming.
  • Suitable solvents for this are, for example, ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate.
  • paranol oils containing butanols according to the invention can be adsorbed on a carrier which ensures both a fine distribution of the odoriferous substances in the product and a controlled release during use.
  • a carrier which ensures both a fine distribution of the odoriferous substances in the product and a controlled release during use.
  • Such supports can be porous inorganic materials such as e.g. Light sulfate, silica gels, zeolites, gypsum, clays, clay granules, gas concrete or organic materials such as wood and cellulose-based substances.
  • parflime oils containing the compounds according to the invention can also be micro-encapsulated, spray-dried, present as inclusion complexes or as extrusion products and added in this form to the product to be perfumed.
  • the properties of the parflime 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 preferably waxy plastics such as Polyvinyl alcohol can be used.
  • microencapsulation of parflime oils can, for example, by the so-called
  • capsule materials e.g. made of polyurethane-like materials or soft gelatin.
  • the spray-dried perfume oils can be produced, for example, by spray drying an emulsion or dispersion containing the parflime oil, and modified starches, proteins, dextrin and vegetable gums can be used as carriers.
  • Complexes can, for example, by adding dispersions of parflime oil and Cyclodextrins or urea derivatives can be prepared in a suitable solvent, for example water.
  • Extrusion products can be made by fusing the perfume oils with a suitable wax-like substance and by extrusion with subsequent solidification, if necessary in a suitable solvent, for example isopropanol.
  • the perfume oils containing the compounds according to the invention can be used in concentrated form, in solutions or in the modified form described above for the production of e.g. Perfume extras, 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, e.g. Floor cleaners, window glass cleaners,
  • Toilet cleaners powder and foam-shaped carpet cleaners, liquid detergents, powder detergents, laundry pretreatment agents such as bleach, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants and air fresheners in liquid, gel-like or on a solid carrier.
  • Aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe creams and personal care products such as solid and liquid
  • the amount of the compounds according to the invention used is 0.05 to 50% by weight, preferably 0.5 to 20% by weight, based on the overall composition.
  • the total amount of the addition products is dissolved in 350 ml of isopropanol and in an autoclave using 2.8 g of ruthenium on activated carbon (moist; water content approx. 50% by weight, Ru content: 5% by weight based on the dry catalyst ) hydrogenated as a catalyst at a hydrogen pressure of 20 bar and a temperature of 150 ° C within 4 hours. It is filtered off from the catalyst and then distilled at 140-150 ° C / 2-3 mbar. 65 g are obtained
  • Isomer 1 222 (14); 166 (47); 111 (40); 97 (79); 83 (77); 69 (63); 55 (100); 41 (54)
  • Isomer 2 222 (21); 166 (63); 111 (41); 97 (79); 83 (84); 69 (70); 55 (100); 41 (60)
  • the fragrance composition is characterized by a longer adhesion.
  • the fresh character of the perfume composition is also supported.
  • Example 4 MIC values / determination of the minimum inhibitory concentration
  • MIC minimum inhibitory concentration

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

Abstract

L'invention concerne des cyclododécylbutan-2-ols, leur utilisation en tant que substances odorantes et en tant qu'agents antimicrobiens, un procédé de fabrication de ces composés, ainsi que des produits contenant lesdits composés.
PCT/EP2003/006878 2002-07-01 2003-06-28 Nouvelles substances odorantes et procede de fabrication Ceased WO2004002930A1 (fr)

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AU2003246631A AU2003246631A1 (en) 2002-07-01 2003-06-28 Odoriferous substances and method for the production thereof

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DE2002129474 DE10229474A1 (de) 2002-07-01 2002-07-01 Neue Riechstoffe und Verfahren zu ihrer Herstellung

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JP2008518198A (ja) * 2004-10-25 2008-05-29 デイド・ベーリング・マルブルク・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング 心血管系疾患のための予知的パラメーターとしてのＰＩＧＦおよびＦｌｔ−１
US9717815B2 (en) 2014-07-30 2017-08-01 Georgia-Pacific Consumer Products Lp Air freshener dispensers, cartridges therefor, systems, and methods

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EP0926121A1 (fr) * 1997-10-28 1999-06-30 Quest International B.V. Réaction d'alcènes avec époxydes, les produits et leur utilisation comme agents de parfum
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JP2008518198A (ja) * 2004-10-25 2008-05-29 デイド・ベーリング・マルブルク・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング 心血管系疾患のための予知的パラメーターとしてのＰＩＧＦおよびＦｌｔ−１
US9717815B2 (en) 2014-07-30 2017-08-01 Georgia-Pacific Consumer Products Lp Air freshener dispensers, cartridges therefor, systems, and methods
US10391193B2 (en) 2014-07-30 2019-08-27 Gpcp Ip Holdings Llc Air freshener dispensers, cartridges therefor, systems, and methods

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AU2003246631A1 (en) 2004-01-19
WO2004002930A8 (fr) 2004-03-18
AU2003246631A8 (en) 2004-01-19
DE10229474A1 (de) 2004-01-15

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