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WO2018192652A1 - 1,1-diméth/éthoxynon-3-ine s'utilisant comme substance odorante - Google Patents

1,1-diméth/éthoxynon-3-ine s'utilisant comme substance odorante Download PDF

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Publication number
WO2018192652A1
WO2018192652A1 PCT/EP2017/059313 EP2017059313W WO2018192652A1 WO 2018192652 A1 WO2018192652 A1 WO 2018192652A1 EP 2017059313 W EP2017059313 W EP 2017059313W WO 2018192652 A1 WO2018192652 A1 WO 2018192652A1
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WIPO (PCT)
Prior art keywords
notes
group
green
odor
fruity
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PCT/EP2017/059313
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German (de)
English (en)
Inventor
Bernd HÖLSCHER
Tobias Wagner
Original Assignee
Symrise Ag
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Priority to PCT/EP2017/059313 priority Critical patent/WO2018192652A1/fr
Publication of WO2018192652A1 publication Critical patent/WO2018192652A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Definitions

  • the present invention primarily relates to the use of 1, 1-dimethoxynon-3-yne and / or 1, 1-diethoxynon-3-yne, i. one or more compound (s) of formula (I) as described herein as a fragrance.
  • the invention additionally relates to novel fragrance compositions comprising 1,1-dimethoxyethoxynon-3-yne, perfumed articles comprising 1,1-dimethoxyethoxynon-3-yne and various processes for imparting, modifying and / or enhancing certain odor notes.
  • fragrances that are able to produce (in fragrance compositions) in addition to a primary fragrance note more interesting notes and to expand the possibilities of the perfumer with their novel or original olfactory properties.
  • odoriferous fragrances which are able to blend harmoniously with floral and / or fruity fragrances.
  • a superposition of the different olfactory aspects and notes take place in order thereby to produce an overall complex olfactory impression.
  • fragrances with special sensory properties which are suitable as a basis for the composition of novel perfumes with complex sensory character to serve.
  • Preferred fragrances sought should have, in addition to a particular note, additional notes and aspects that give them character and complexity.
  • fragrances which have an interesting, preferably complex, and original sensory profile and are useful as fragrances for use in e.g. the perfumery or other areas, possibly even in edible preparations.
  • substances which have one, several or all of the notes green, floral and woody, or can mediate, modify and / or enhance them.
  • substances should be found which preferably have at least one of the notes green and (strong) violet note and / or can mediate.
  • the sought-after substances should enable the production of novel fragrance compositions with special odor notes and aspects. Of advantage would be those substances which are particularly suitable for combination with other fragrances that have one or more of the notes green and / or (strong) violet note.
  • the fragrances which fulfill this primary function should preferably have additional positive secondary properties beyond their primary, namely odoriferous properties, such as high stability under certain conditions of use, high yield, good adhesion, high substantivity or odor-enhancing properties (so-called booster properties). or enhancer effect) and / or in combination with other fragrances their naturalness, freshness, fullness, (beam) power and / or radiation round off, so that sensory effects can be achieved.
  • the primary object is achieved by the use of 1, 1-dimethoxynone-3-in (formula (Ia), szB CAS No. 87745-62-8) and / or 1, 1-diethoxynon-3-in ( Formula (Ib), see, for example, CAS No. 90290-02-1), ie one or more or both compounds of the formula (I), where the radicals R 1 and R 2 are either both methyl or both ethyl (1, 1-Dimeth / ethoxynon-3-in),
  • the use of the invention relates to a use for imparting, modifying and / or enhancing one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, greasy, metallic and balsamic, preferably one or more of the odor notes selected from the group consisting of the notes green, woody, fruity and floral, more preferably one or more of the odor notes selected from the group consisting of the notes green and violet.
  • a preferred embodiment relates to the use of one or more compound (s) of formula (I) as described herein for imparting one, two or more odorants selected from the group consisting of the green and (strong) violet notes.
  • a compound of the formula (I) to be employed according to the invention may impart a very complex and varied overall sensory impression which otherwise can usually only be achieved by mixtures of several components (such as, for example, essential oils or spice mixtures) is particularly surprising.
  • the compounds of the formula (I) additionally have positive secondary properties, in particular good adhesion and high substantivity in comparison with odoriferous substances having similar odor properties, and high stability in certain media and preparations In addition, they are biodegradable and biodegradable.
  • a compound of the formula (I) to be used according to the invention has very excellent stability, especially in the neutral, but in particular in the alkaline range.
  • the compounds of formula (I) are excellently suited for use as perfumes, especially when used in perfumed articles or formulations having a pH of 7 or greater, more preferably greater than 7 , 5, in particular preferably greater than 8; furthermore in oxidizing preparations which preferably have a pH of greater than or equal to 7, preferably in oxidizing preparations having a pH of greater than or equal to 8.
  • the indicated pH values in each case relate to measured at 25 ° C. Values.
  • a compound of the formula (I) can function excellently as a so-called booster (enhancer).
  • a compound of the formula (I) to be used according to the invention can enhance the intensity of a fragrance mixture (fragrance composition) and round off the overall appearance of the mixture in the odor.
  • the compounds described herein can therefore be used to impart more fullness, freshness, (beam) power, aura, shine, roundness, harmony, and / or naturalness to a fragrance composition.
  • the preparation of a compound of the formula (I) to be used according to the invention can be carried out by means of known reactions and processes.
  • alkylation in the basic of heptin-1 with chloroacetaldehyde dimethyl acetal or chloroacetaldehyde diethyl acetal can produce a compound of the formula (I), ie a compound of the formula (Ia) or (Ib), under appropriate conditions.
  • a compound of the formula (I) can be prepared by isomerization of 1,1-dimethoxynone-2-yne or 1,1-diethoxynon-2-yne (1,1-dimethoxyethoxynon-2-yne) with the aid of potassium tert-butylate are prepared (the educts used for it are commercially available).
  • a compound of the formula (I) to be used according to the invention is usually employed in a sensory effective amount in the context of the use according to the invention, ie in a total amount in which it develops a sensory effect.
  • a compound of the formula (I) to be used according to the invention is used together with other fragrances.
  • Such fragrance compositions can be prepared in the usual way, for example by simply mixing or homogenizing the constituents. These other fragrances can be any other fragrance.
  • a further aspect of the present invention therefore relates to a fragrance substance composition
  • a fragrance substance composition comprising or consisting of one or more compound (s) of the formula (I)
  • radicals R- 1 and R 2 are either both methyl or both ethyl, and one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance (s), wherein the weight ratio of the total amount to compound (s) of formula (I) to the total amount of further perfume (s) in the range of 1: 1000 to 1: 0.1, preferably from 1: 1000 to 1: 0.5.
  • the total amount of compound (s) of the formula (I), based on the total weight of the perfume composition in the range of 0.0001 to 99.9 wt .-%, preferably 0.001 to 99.5 wt. %, particularly preferably 0.01 to 99 wt .-%, 0.01 to 90 wt .-%, 0.05 to 80 wt .-%, 0.1 to 70 wt .-%, 0.25 to 50 wt .-%, 0.5 to 40 wt .-% or 0.75 to 25 wt .-%, is.
  • the total amount of the Compound of formula (I) are also chosen to be comparatively low and, for example, preferably in the range of 0.01 to 5 wt .-%, more preferably in the range of 0.1 to 2 wt .-%, based on the total amount of the fragrance composition, are , If within the preferred Concentration ranges a comparatively low concentration is selected, it may not come in accordance with the other components of the composition in some cases, the mediation of the above-mentioned self-odor notes. Thus, depending on the desired effect of a compound of the formula (I), the person skilled in the art can select a suitable amount of compound (s) of the formula (I) for the particular application.
  • a compound of the formula (I) is outstandingly suitable for use in fragrance substance compositions according to the invention.
  • a compound of formula (I) may advantageously be combined with a variety of other fragrances and used in numerous different products and articles.
  • the total amount of compound (s) of formula (I) in the fragrance composition is contained in a sensory effective amount, preferably in an amount sufficient to produce one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, greasy, metallic and balsamic, preferably at least one of the odor notes selected from the group consisting of the notes green, woody, fruity and floral, particularly preferably at least one of Odor notes selected from the group consisting of the green and violet notes, to be conveyed and / or amplified and / or to modify one or more odor notes of one or more of the perfume (s) of the perfume composition towards one or more of these odor notes.
  • the one or more, or all of the further fragrances also) one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy greasy, metallic and balsamic, preferably one or more of the odor notes selected from the group consisting of the notes green, woody, fruity and floral, more preferably selected from the group consisting of the notes green and violet, impart, modify and / or reinforce or (ii) one or more or all of the other fragrances mediate, modify and / or enhance one or more odor notes other than those mentioned in (i).
  • fragrances which can be advantageously combined in the context of the present invention with a compound of the formula (I) are found, for example, in US Pat. See, for example, S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, Eigenverlag, or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001.
  • extracts from natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balsams, tinctures such.
  • 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; Cascarillaöl;
  • citronella lemon; copaiba balsam; Copaivabalsamöl; Coriander oil; costus root;
  • Fennel oil Pine needle oil; galbanum; Galbanumresin; geranium; Grapefruit oil;
  • Ginger oil Iris root absolute; Orris root oil; Jasmine absolute; calamus; Chamomile oil blue;
  • Camomile oil Roman; Carrot seed oil; Kaskarillaöl; Pine needle oil; spearmint; Seed oil; labdanum; Labdanum absolute; Labdanumresin; Lavandin absolute;
  • Opopanaxöl Orange blossom absolute; Orange oil; oregano; Palmarosa oil; patchouli oil;
  • perilla oil Peruvian balsam oil; Parsley leaf oil; Parsley seed oil; Petitgrain oil;
  • Peppermint oil Pepper oil; chilli; pine oil; Poleyöl; Rose absolute; Rosewood oil; Rose oil;
  • Rosemary oil Rosemary oil; Sage oil Dalmatian; Sage oil spanish; sandalwood; Celery seed oil; spike lavender oil; star anise; Styraxöl; tagetes; Pine needle oil; Tea-tree-oil;
  • fragrances from the group of hydrocarbons such as 3-carene; ⁇ -pinene; ⁇ -pinene; a-terpinene; ⁇ -terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -1, 3,5-undecatriene; styrene; diphenylmethane;
  • the aliphatic alcohols such as e.g. hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; 1-octene-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 e.g. hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; 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;
  • the aliphatic ketones and their oximes 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-octene-3-one; 6-methyl-5-hepten-2-one;
  • aliphatic sulfur-containing compounds e.g. 3-methylthio-hexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3
  • aliphatic nitriles e.g. 2-nonenoic acid nitrile; 2-Undecenhoffrenitril; 2-tridecenoic acid nitrile; 3,12-tridecadienoic acid nitrile; 3,7-dimethyl-2,6-octadiene-acid nitrile; 3,7-dimethyl-6-octenoic acid nitrile;
  • ester of aliphatic carboxylic acids e.g. (E) - and (Z) -3-hexenylformate; ethylacetoacetate; isoamyl; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenylacetate; octyl acetate; 3-octyl acetate; 1-octene-3-yl acetate; ethyl butyrate; butyl butyrate; isoamyl; hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate; hexyl crotonate; Ethylisovalerianat; Ethyl 2-methylpentanoate; ethylhexanoate; allyl hexanoate; e
  • cyclic alcohols e.g. 4-tert.-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-lsocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol;
  • the cycloaliphatic alcohols e.g. alpha, 3,3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-Dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1- (2,2,6-trimethylcyclohexyl) pentan-3-ol; 1- (2,2,6-trimethylcyclohexyl) hexan-3-ol;
  • the cyclic and cycloaliphatic ethers such as cineole; cedryl methyl ether; Cyclododecyl methyl ether; 1, 1-dimethoxycyclododecane; (Ethoxymethoxy) cyclo dodecane; alpha-Cedrenepoxid; 3a, 6,6,9a-tetramethyldodecahydro-naphtho [2, 1-b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2, 1 b] furan; 1, 5,9-tri-methyl-13-oxabicyclo [10.1.0] trideca-4,8-diene; rose oxide; 2- (2,4-dimethyl-3-cyclohexen-1-yl) -5-methyl-5- (1-methylpropyl) -1,3-doxan; the cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl
  • Cycloheptadecen-1- ⁇ cyclopentadecanone; cyclohexadecanone;
  • cycloaliphatic aldehydes e.g. 2-methyl-4- (2,2,6-trimethylcyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexenecarbaldehyde;
  • ester of cyclic alcohols e.g. 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentyl-cyclo-hexyl acetate; 3,3,5-tri methylcyclohexyl acetate; Decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-yl acetate; Decahydro-2,5,5,8-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexa-hydro-5, and 6-indenyl acetate, respectively; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indeny
  • ester of cycloaliphatic alcohols such as 1-cyclohexylethyl crotonate
  • esters of cycloaliphatic carboxylic acids such as.
  • allyl-3-cyclohexylpropionate Allylcyclohexyloxyacetat; cis and trans methyldihydrojasmonate; egg and trans methyl jasmonate;
  • Methyl-2-hexyl-3-oxocyclopentanecarboxylate Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexene carboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexene-carboxylate; Ethyl 2-methyl-1,3-dioxolane-2-acetate;
  • the aliphatic alcohols such as benzyl alcohol; 1-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-phenyl-propanol; 2-Methyl-5- phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl alcohol; 1- (4-isopropylphenyl) ethanol;
  • ester of araliphatic alcohols and aliphatic carboxylic acids e.g. benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-Phenylethylisobutyrat; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-dimethylphenylethyl acetate; alpha, alpha-Dimethylphenylethylbutyrat; cinnamyl; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
  • the aliphatic ether such as e.g. 2-phenylethyl; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether; phenylacetaldehyde; phenylacetaldehyde; Hydratropaaldehyddimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetra-hydroindeno [1,2-d] -m-dioxin; 4,4a, 5,9b-tetrahydro-2,4-dimethylindo [1,2-d] -m-dioxin; the aromatic and aliphatic aldehydes such.
  • aromatic and aliphatic ketones e.g. acetophenone; 4-methylacetophenone;
  • aromatic and aliphatic carboxylic acids and their esters such as benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethylcinnamat; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; benzyl; phenylethyl; Methyl- 2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenylglycidate; Ethyl 3-phenylglycid
  • the nitrogen-containing 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; cinnamic acid; 3-methyl-5-phenyl-2-pentenoic acid nitrile; 3-methyl-5-phenylpentan-acid nitrile; methyl anthranilate; Methyl N-methylanthranilate; Schiff's bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexene carbaldehyde; 6-isopropyl-quinoline; 6-lsobutylchinolin; 6-sec-butylquinoline; 2- (3-phenylpropyl) pyridine; indole; skatol; 2-me
  • the phenols, phenyl ethers and phenyl esters e.g. estragole; anethole; Eugenylmethylether; isoeugenol; Isoeugenylmethylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-naphthylisobutyl ether; 1, 4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methyl phenol; 2-ethoxy-5- (1-propenyl) phenol; p-Kresylphenylacetat;
  • heterocyclic compounds such as e.g. 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-one;
  • the lactones e.g. 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decene-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1, 5-decanolide; 1, 5-dodecanolide; 4-methyl-1,4-decanolide; 1,15-pentadecanolide; 1, 16-hexadeca-nolide; 9-hexadecene-1, 16-olide; 10-oxa-1, 16-hexadecanolide; 1 1-oxa-1,16-hexa-decanolide; 12-oxa-1, 16-hexadecanolide; Ethylene-1,12-dodecanedioate; Ethylene-1,13-tridecanedioate; 2,3-dihydrocoumarin; Octahydrocoumarin.
  • a compound of the formula (I) to be used according to the invention is preferably combined with one or more, more preferably two, three, four, five or more further fragrances which have a floral and / or fruity odor note.
  • the present invention also relates to a fragrance composition
  • a fragrance composition comprising one, two, three, four, five or more further fragrances which impart a flowery and / or fruity scent note.
  • a compound of the formula (I) to be used according to the invention advantageously (at least in part) an odoriferous enhancement of the flowery fragrances is achieved.
  • a compound of the formula (I) to be used according to the invention is advantageously suitable for intensifying, in particular, fruity fragrances with regard to their odor.
  • Fruity fragrances with which the compounds of the formula (I) to be used according to the invention can advantageously be combined, and which are therefore particularly preferred (further) fragrances of a fragrance substance compositions according to the invention, are preferably selected from the group consisting of: Ethyl 2-methylbutyrate, 4- (p-hydroxyphenyl) -2-butanone, ethyl 3-methyl-3-phenylglycidate, isobutyric butyrate, isoamyl acetate, n-butyl acetate, ethyl butyrate, ethyl 3-methylbutyrate, n-butyl
  • Fragrance compositions according to the invention which contain a compound of the formula (I) can be diluted in liquid form, neat or with a solvent and advantageously be used for perfuming.
  • Preferred solvents for this are ethanol, isopropanol, diethylene glycol monoethyl ether, glycerol, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin and diacetin.
  • fragrance compositions of the present invention may be adsorbed to a carrier which provides both for a fine distribution of the fragrances in the product and for controlled release in use.
  • a carrier may be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc. or organic materials such as woods, cellulosic based substances, sugars, dextrins (e.g., maltodextrin), or plastics such as PVC, polyvinyl acetates or polyurethanes.
  • inventive composition and carrier is also to be understood as fragrance composition according to the invention or may be present as inventive article (as described herein below).
  • Perfume compositions or articles may also be microencapsulated, spray dried, included as inclusion complexes or as extrusion products and, in the case of a fragrance composition, in this form, e.g. to be added to a product to be perfumed (as further described below).
  • compositions or articles modified in this way can be further optimized by so-called "coats" with suitable materials with a view to a more targeted release of fragrance, for which purpose waxy plastics such as polyvinyl alcohol are preferably used.
  • Microencapsulation can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, for example of polyurethane-type substances or soft gelatin.
  • Spray-dried products are preferably prepared by spray-drying an emulsion or dispersion containing the fragrance composition, it being possible to use as excipients modified starches, proteins, dextrin and vegetable gums.
  • Inclusion complexes can be e.g. by incorporating dispersions of the fragrance composition and cyclodextrins or urea derivatives into a suitable solvent, e.g. Water, to be produced.
  • a suitable solvent e.g. Water
  • Extrusion products can e.g. by fusing the perfume compositions with a suitable waxy substance and by extrusion followed by solidification, optionally in a suitable solvent, e.g. Isopropanol.
  • a suitable solvent e.g. Isopropanol.
  • Another aspect of the present invention relates to the use of a fragrance composition according to the invention for imparting, modifying and / or enhancing one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, greasy, metallic and balsamic, preferably at least one of the odor notes selected from the group consisting of the notes green, woody, fruity and floral, more preferably at least one of the odor notes selected from the group consisting of the notes green and violet.
  • Fragrance compositions according to the invention can advantageously be used in concentrated form, in solutions or in modified form as described above for the production of perfumed articles according to the invention, such as e.g.
  • Another aspect of the present invention relates to a method of imparting, enhancing and / or modifying one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, greasy, metallic and balsamic , preferably for imparting, enhancing and / or modifying one or more odor notes selected from the group consisting of the notes green, woody, fruity and floral, more preferably for imparting, enhancing and / or modifying one or more odor notes selected from the group consisting of the notes green and violet, comprising or consisting of the following steps: (a) Provide
  • fragrances having one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity , flowery, woody, sweet, earthy, greasy, metallic and balsamic, preferably with one or more odor notes selected from the group consisting of the notes green, woody, fruity and floral, more preferably with one or more odor notes selected from the group consisting of the notes green and violet,
  • Another aspect of the present invention relates to a perfumed article comprising or consisting of
  • a fragrance composition as described herein, or one or more compound (s) of formula (I) wherein the radicals R- 1 and R 2 are either both methyl or both ethyl, and one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance (s), wherein the weight ratio of the total amount compound (s) of formula (I) to the total amount of further perfume (s) in the range of 1: 1000 to 1: 0.1, preferably from 1: 1000 to 1: 0.5, and
  • one or more further constituents preferably at least one or more, preferably one, two, three, four, five or more, additional, auxiliary and / or active ingredient (s).
  • radicals R 1 and R 2 are either both methyl or both ethyl, preferably in a sensorially effective amount which is sufficient to impart, enhance and / or modify one or more of the odor notes green and / or violet and / or to reinforce, and one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance (s), wherein the weight ratio of the total amount of compound (s) of formula (I) to the total amount of further fragrance (s) in the range from 1: 1000 to 1: 0, 1, preferably from 1: 1000 to 1: 0.5, and preferably wherein one, several or all of the further fragrances impart a woody, fruity and / or floral odor, and
  • one or more further constituents preferably at least one or more, preferably one, two, three, four, five or more, additional, auxiliary and / or active ingredient (s).
  • an inventive article is selected from the group consisting of detergents and cleaners, hygiene or care products, preferably in the field of body and hair care, cosmetics and household, preferably from the group consisting of perfume solutions, Eau de perfume , Eau de toilettes, shaving lotions, eau de colognes, pre-shave products, splash colognes, perfumed towelettes, acidic, alkaline or neutral detergents, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pre-treatment preparations, fabric conditioners, laundry soap, washing tablets, disinfectants , Surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products, deodorants, antiperspirants, pr odukte of decorative cosmetics, candles, lamp oils, incense, insecticides, repellents
  • ingredient (i) be contained in a sensory effective amount, preferably in an amount sufficient for a consumer to have one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh , fruity, flowery, woody, sweet, earthy, greasy, metallic and balsamic, preferably one or more odor notes selected from the group consisting of the notes green, woody, fruity and floral, more preferably one or more odor notes selected from the group consisting of the notes green and violet, perceives.
  • the total amount of compound (s) of formula (I), based on the total weight of the article is in the range from 0.00001 to 10% by weight, preferably 0.0001 to 5% by weight, more preferably 0.001 to 2% by weight, more preferably 0.005 to 1% by weight.
  • the additives, auxiliaries and / or active substances described above are preferably not fragrances and, if present, are preferably selected from the group consisting of:
  • Preservatives preferably the abrasives, anti-acne agents and sebum reduction agents mentioned in US 2006/0089413, preferably the anti-aging agents mentioned in WO 2008/046791, preferably the antibacterial agents, anti-cellulitis agents mentioned in WO 2005/123101, Anti-dandruff agents, preferably the anti-inflammatory agents mentioned in WO 2008/046795, anti-irritants, anti-irritants (antiinflammatory, anti-irritant and anti-irritant agents), preferably the antimicrobial agents mentioned in WO 2007/042472 and US 2006/0089413, preferably those in WO 2005/123101, preferably the excipients, antiseptics, antistatic agents, binders, buffers, carrier materials mentioned in WO 2005/123101, preferably the chelating agents mentioned in WO 2005/123101, preferably the cell stimulants mentioned in WO 2005/123101 , cleansers, nourishing, depilatory, surface-active Substances, deodorants and antiperspirants, preferably
  • moisturizing, moisturizing and / or moisturizing substances preferably the osmolytes mentioned in WO 2005/123101, preferably the compatible solutes mentioned in WO 2005/123101, preferably the bleaching agents mentioned in WO 01/76572 and WO 02/15686, fortifying agents, stain removers, optically brightening agents, waterproofing e agents, antisoiling agents, friction-reducing agents, lubricants, moisturizing creams, ointments, opacifiers, plasticizers, covering agents, polishes, brighteners, polymers, preferably the powders, proteins and protein hydrolysates mentioned in WO 2008/046676, preferably those described in WO 2005 / 123101 and WO 2008/046676, emollients, abrasives, skin soothing agents, skin cleansers, skin care agents, Skin-repairing agents (skin repair agents), preferably containing cholesterol and / or fatty acids and / or ceramides and / or pseudoceramide
  • dicarbonyl compounds preferably the alpha-benzoylcinnamic acid nitriles mentioned in WO 2005/107692, preferably the AhR receptor antagonists mentioned in WO 2006/015954, preferably the detergents, fabric softeners, suspending agents mentioned in WO 2007/128723 and WO 2007/060256 , Skin tanning agents, preferably the thickeners, vitamins, mentioned in WO 2006/045760, preferably those mentioned in WO 2005/123101, f fatty acids (saturated fatty acids, mono- or polyunsaturated fatty acids, hydroxy acids, polyhydroxy fatty acids) 123101, dyes and color-protecting agents and pigments, preferably those mentioned in WO 2005/123101, anticorrosives, alcohols and polyols, preferably the surfactants mentioned in WO 2005/123101, preferably the animal extracts mentioned in WO 2005/123101, yeast extracts, Extracts of algae or microalgae, electrolytes, plasticizers, organic solvents, organic
  • radicals R- 1 and R 2 are either both methyl or both ethyl, and optionally one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance (s), wherein the weight ratio of Total amount of compound (s) of formula (I) to the total amount of further perfume (s) in the range of 1: 1000 to 1: 0, 1, preferably from 1: 1000 to 1: 0.5, and
  • fragrance composition (a.1) or the compound (s) / fragrances (a.2) to the article to be perfumed, in a sensory effective amount, preferably in an amount sufficient to one or more odor notes selected from the group consisting of the notes green, herbaceous, fresh, fruity, floral, woody, sweet, earthy, greasy, metallic and balsamic, preferably one or more of the aromas selected from the group consisting of the notes green, woody, fruity and flowery, more preferably one or more of the odor notes selected from the group consisting of the notes green and violet, to convey, reinforce and / or modify.
  • the present invention relates to a method for perfuming hair, skin, textile fibers, surfaces and / or room air comprising or consisting of the following steps:
  • a perfume composition according to the invention (as described herein), preferably containing a surfactant or a surfactant mixture, or
  • radicals R- 1 and R 2 are either both methyl or both ethyl, and optionally one, two, three, four, five, six, seven, eight, nine, ten or more further fragrance (s), wherein the weight ratio of Total amount of compound (s) of formula (I) to the total amount of further perfume (s) in the range of 1: 1000 to 1: 0, 1, preferably from 1: 1000 to 1: 0.5, and furthermore preferably a surfactant or a surfactant mixture, or
  • radical R- ⁇ methyl and the radical R 2 is ethyl, and their use as a fragrance.
  • the said compound of the formula (I) can be present or used as any stereoisomer or as a mixture of stereoisomers.
  • radical R- ⁇ methyl and the radical R 2 is ethyl
  • the radicals Ri and R 2 either both methyl or both ethyl
  • DPG dipropylene glycol
  • TEC triethyl citrate
  • this perfume composition becomes stronger, more rounded and softer by the addition of 0.2% by weight of the compound of the formula (Ia) (eg product of Example 1), with clear aspects in the floral direction being added.
  • the compound of formula (la) gives the composition its own character and combines the different odoriferous elements.
  • this perfume composition alternatively becomes stronger, rounder and softer, with a marked floral note, by the addition of 0.3% by weight of the compound of formula (Ib).
  • the compound of the formula (Ib) gives the composition its own character in the direction of naturalness.
  • this perfume composition is awakened by the addition of 0.2% by weight of a compound of the formula (Ia) (eg product of Example 1, 10% strength in DPG).
  • a compound of the formula (Ia) eg product of Example 1, 10% strength in DPG.
  • the impression of raspberry is clearly enhanced.
  • the composition looks fresher and more rounded, adding a natural touch.
  • this perfume composition alternatively awakens by the addition of 0.3% by weight of the compound of formula (Ib) (10% in DPG).
  • the impression of fruit is clearly enhanced.
  • the composition looks fresher and more rounded in the direction of wild raspberry with a natural touch.
  • Example 1 The product of Example 1 to be used according to the invention was incorporated in a dosage of 0.5% by weight into a shampoo base of the following composition:
  • Citric acid 1 3%
  • the pH of the shampoo base was about 6. From this, 100 ml of a 20 wt .-% aqueous shampoo solution were prepared. In this shampoo solution, two hair tresses were washed together for 2 minutes and then rinsed for 20 seconds under running lukewarm water. One strand of hair was wet wrapped in aluminum foil and dried the second strand of hair with a hair dryer. Both strands of hair were judged by a panel odor.
  • Example 2 The perfume composition from Example 2 (after addition of 6% by weight of the product from Example 1) was incorporated in a dosage of 0.5% by weight into a fabric softener base of the following composition:
  • the fabric softener base pH was in the range of 2 to 3. Two pieces of fabric were mixed with 370 g of a 1% aqueous fabric softener solution based on the fabric softening solution containing 0.2% by weight of the perfume composition of Example 2. Base mass in a Linetest machine in the softening program 30 minutes at 20 ° C rinsed. The flaps were wrung out and then spun for 20 seconds. A rag was wet-welded, and one hung up to dry. Subsequently, both flaps were assessed by a panel odor.
  • Example 3 The perfume oil composition from Example 3 (after addition of 0.5% by weight of the product from Example 1, 10% strength in DPG) was incorporated in a dosage of 0.4% by weight into a base powder of the following formulation:
  • Odor description each: a beautiful fruity raspberry note with woody undertone is perceive.
  • the perfume composition looks rounded, harmonious, with a natural touch.

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

Abstract

La présente invention concerne en premier lieu l'utilisation de 1,1-diméth/éthoxynon-3-ine comme substance odorante. L'invention concerne également de nouvelles compositions de substances odorantes comprenant 1,1-diméth/éthoxynon-3-ine et leur utilisation, des articles parfumés contenant 1,1-diméth/éthoxynon-3-ine ainsi que divers procédés permettant de fournir, modifier et/ou renforcer des notes odorantes déterminées.
PCT/EP2017/059313 2017-04-19 2017-04-19 1,1-diméth/éthoxynon-3-ine s'utilisant comme substance odorante WO2018192652A1 (fr)

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