WO2007065755A1 - 2-methoxymethylphenol as perfume and aroma substance - Google Patents

2-methoxymethylphenol as perfume and aroma substance Download PDF

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Publication number
WO2007065755A1
WO2007065755A1 PCT/EP2006/067646 EP2006067646W WO2007065755A1 WO 2007065755 A1 WO2007065755 A1 WO 2007065755A1 EP 2006067646 W EP2006067646 W EP 2006067646W WO 2007065755 A1 WO2007065755 A1 WO 2007065755A1
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WO
WIPO (PCT)
Prior art keywords
methoxymethylphenol
fragrance
ester
oil
methyl
Prior art date
Application number
PCT/EP2006/067646
Other languages
German (de)
French (fr)
Inventor
Johannes Panten
Axel Schöning
Thomas Obrocki
Bernd Wiedwald
Original Assignee
Symrise Gmbh & Co. Kg
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Publication date
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Publication of WO2007065755A1 publication Critical patent/WO2007065755A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50Perfumes
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • A23L27/204Aromatic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B9/00Essential oils; Perfumes
    • C11B9/0061Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2068Ethers

Definitions

  • the present invention relates primarily to the use of 2-methoxymethylphenol as a fragrance or aroma substance with a vanilla, carnation and / or leathery note.
  • the invention also relates to the use of 2-methoxymethylphenol as a booster (enhancer) for fragrance or flavoring substances, in particular for fragrance or flavoring substances with fresh, fruity and / or sweet notes.
  • the invention further relates to certain methods for imparting, modifying and / or enhancing (boosting) an odor or taste with one, several or all of the notes vanilla, clove-like and / or leathery, and methods for modifying and / or enhancing (boosting) a smell and / or taste with one, several or all of the notes fresh, fruity and / or sweet.
  • the invention also relates to certain fragrance or flavoring compositions which
  • 2-Methoxymethylphenol include and processes for the preparation of corresponding fragrance or flavoring compositions.
  • the invention also relates to a Product comprising a fragrance or flavoring composition according to the invention (for preferred product types see below).
  • the invention also relates to the use of 2-methoxymethylphenol or a mixture containing 2-methoxymethylphenol as an agent for providing (a) hair or (b) textile fibers with a vanilla, carnation and / or leathery fragrance and corresponding methods and (preferably surfactant-containing) Mixtures.
  • the invention also relates to the use of 2-methoxymethylphenol as an agent for increasing the substantivity and / or retention of an odorant mixture and / or as a fixator and the use of 2-methoxymethylphenol as an agent for increasing the odor of other odorants perceived via a surfactant-containing aqueous solution .
  • the invention also relates to methods for providing (a) hair or (b) textile fibers with a fruity, fresh and / or sweet smell.
  • the invention also relates to products containing 2-methoxymethylphenol and in addition, for. B. include other fragrances and / or surfactants.
  • fragrances which, in addition to their primary, namely odor properties, have additional positive secondary properties, such as, for example, greater stability under certain application conditions, higher yield, better quality Adhesion, a greater charisma or better dermatological and toxicological properties compared to comparable fragrances, such as good biodegradability.
  • additional positive secondary properties such as, for example, greater stability under certain application conditions, higher yield, better quality Adhesion, a greater charisma or better dermatological and toxicological properties compared to comparable fragrances, such as good biodegradability.
  • concerns about some of the commonly used fragrances have been raised regarding the latter properties. It is to be expected that their use will be limited in the future or that the use will have to be dispensed with entirely.
  • perfume industry for further fragrances which are suitable for producing fragrance compositions or perfumed articles.
  • odoriferous substances which, due to the technical properties mentioned above, such as strength or yield, lead to an increased use of perfume oils.
  • the present invention relates to the use of 2-methoxymethylphenol as a fragrance or aroma substance with a vanilla, carnation and / or leathery note.
  • Another aspect of the present invention relates to the use of 2-methoxymethylphenol as a booster for fragrance or flavoring substances, in particular for fragrance or flavoring substances with fresh, fruity and / or sweet notes.
  • 2-methoxymethylphenol enhances the smell or taste of odoriferous or aromatic substances, especially fresh, fruity and / or sweet notes.
  • the so-called “boost effect” is particularly pronounced in perfume oils, especially perfume oils with fruity, fresh and / or sweet notes.
  • 2-methoxymethylphenol is outstandingly suitable for enhancing (boosting) an odor or taste with fruity, fresh and / or sweet notes.
  • This property of 2-methoxymethylphenol is illustrated using a perfume oil with a fruity raspberry note in Example 2 (see below).
  • particularly good results were obtained when 2-methoxymethylphenol was combined with one or more of the compounds listed in Table 2.
  • 2-methoxymethylphenol is used as a fragrance or aroma substance with a vanilla, carnation and / or leathery note.
  • a corresponding method according to the invention for imparting, modifying and / or enhancing (boosting) an odor or taste with one, several or all of the notes vanilla, clove-like and / or leathery comprises a step in which a quantity of 2-methoxymethylphenol or a 2-methoxymethylphenol comprehensive fragrance or flavoring composition is brought into contact with a product or mixed.
  • the product can be, for example, a further fragrance or flavoring substance or a mixture of other fragrance or flavoring substances.
  • a corresponding method for modifying and / or enhancing (boosting) an odor and / or taste with one, several or all of the notes fresh, fruity and / or sweet comprises the following step:
  • the 2-methoxymethylphenol to be used according to the invention is able to intensify the intensity of the fragrance or aroma substance mixture even in small doses and to round off the overall appearance of the mixture and to give the mixture more radiance, gloss, harmony and naturalness to lend.
  • Fragrance or flavoring compositions which comprise 2-methoxymethylphenol and one or more further fragrance or flavoring substances (in particular fragrance or flavoring substances with a fruity, fresh and / or sweet note) have a surprising olfactory quality.
  • the invention also relates to corresponding fragrance or flavoring compositions which comprise 2-methoxymethylphenol and one or more further fragrance or flavoring substances.
  • At least three different types of fragrance or flavoring compositions according to the invention can be distinguished from one another, although the transitions from one type to the other are fluid.
  • type (i) of a fragrance or aroma composition according to the invention the amount of 2-methoxymethylphenol is sufficient to impart one, more or all of the notes vanilla, clove-like and / or leathery.
  • composition (i) exists in particular when none of the other fragrance or aroma substances itself conveys one, several or all of the notes vanilla, carnation and / or leathery, but the amount of 2-methoxymethylphenol is sufficient to convey one, several or all of these notes.
  • the further fragrance or flavoring agent (s) impart one, several or all of the notes vanilla, clove-like, leathery, fresh, fruity and / or sweet and the amount of 2-methoxymethylphenol is sufficient, modify and / or reinforce (to boost) one or more of these notes.
  • the amount of 2-methoxymethylphenol is sufficient to give the fragrance or flavoring composition (out) radiation, gloss, roundness, naturalness and / or harmony.
  • fragrance or flavoring compositions according to the invention which, in addition to the 2-methoxymethylphenol to be used according to the invention, contain one or more further fragrance or flavorings which are selected from the group consisting of:
  • compositions comprising 2-methoxymethylphenol and one or more further odoriferous or aromatic substances selected from the group consisting of 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl-3-methyl-3- phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1, 1-dimethoxy-2,2 5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, gamma-undecalactone, and gamma-nonalactone, ie
  • fragrance or flavoring compositions according to the invention which contain an amount of 2-methoxymethylphenol in the range from 0.0001 to 90% by weight, preferably 0.01 to 70% by weight and particularly preferred 0.1 to 50 wt .-%, based on the total amount of the fragrance or flavoring composition.
  • 2-methoxymethylphenol is mainly used to give a fragrance or aroma composition more radiation, shine, roundness, naturalness and / or harmony and / or to modify or reinforce certain notes, especially notes of the fruity, fresh and / or sweet
  • the proportion of 2-methoxymethylphenol is preferably quite low and preferably in the range from 0.01 to 5% by weight, preferably in the range from 0.1 to 2% by weight, based on the total amount of odoriferous or Flavor composition. If a comparatively low concentration is selected within the preferred concentration ranges, depending on the other components of the respective composition, the intrinsic odor or taste notes given above are not conveyed in some cases.
  • Fragrance or flavoring compositions according to the invention are preferably used for the production of perfumed or flavored products (articles); for preferred perfumed or flavored products see below.
  • the sensory properties, material properties (such as solubility in common solvents and compatibility with other common constituents of such products) and the toxicological harmlessness of the compound to be used according to the invention underline their particular suitability for the purposes mentioned.
  • Fragrance or flavoring compositions according to the invention are particularly preferred in which the effects of types (i), (ii) and (iii) occur side by side and overlapping one another.
  • An example of such a preferred fragrance composition (perfume composition) is given in Example 2 below.
  • a fragrance or flavoring composition according to the invention is produced according to the invention by mixing 2-methoxymethylphenol with customary further constituents of a fragrance or flavoring composition, the 2-methoxymethylphenol being used in an amount sufficient to provide an odor in the fragrance or flavoring composition. or to convey, modify and / or reinforce taste.
  • the example of a "fruity-vanilla raspberry" fragrance composition given below clearly demonstrates the olfactory effect of 2-methoxymethylphenol.
  • the usual components are included the olfactory or aroma substance composition olfactory or aroma substances, which are selected from the group already mentioned above, which consists of: 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl-3-methyl-3- phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1, 1-dimethoxy-2,2-dimethoxy 5-trimethyl-4-hexane,
  • the compounds 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl 3-methyl-3-phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl are particularly preferred -butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1, 1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-heptene -1-al, gamma undecalactone, gamma-nonalactone and mixtures thereof.
  • the invention also relates to the use of 2-methoxymethylphenol as an agent for increasing the substantivity and / or retention of a fragrance mixture (fragrance composition) and / or as a fixator.
  • Fragrance mixtures containing 2-methoxymethylphenol or 2-methoxymethylphenol are characterized by a high absorbency (self-adhesion on a substrate) and a high substantivity (ability to absorb from a, usually aqueous, phase onto a substrate or also after a washing or rinsing process to remain on a substrate). This effect is particularly evident on substrates such as skin, hair and textile fibers (e.g. wool, cotton, linen, synthetic fibers).
  • perfumed products according to the invention are therefore detergents, hygiene or care products, in particular in the field of body and hair care, cosmetics and the household.
  • fragrances and fragrance mixtures are their substantivity towards or retention on the substrate, in particular hair or textile fibers.
  • substantially and retention are e.g. detailed in EP 1 201 738 A1, cf. there the sections [0004] - [0005]. Fragrance substances with high substantivity and / or retention are therefore also generally sought.
  • a fruity, fresh and / or sweet-scented for example, a fruity, fresh and / or sweet-scented, but due to insufficient substantivity of the fragrances contained, not suitable for passing on a fruity, fresh and / or sweet smell to laundry (textile fibers) or hair, an aqueous washing solution (or a Corresponding detergent or shampoo or the like) by adding 2-methoxymethylphenol into a solution that excellently transmits a fruity, fresh and / or sweet smell - and the fruity, fresh and / adheres to the treated substrates (hair or textile fibers) or sweet smell for a long time.
  • an aqueous washing solution or a Corresponding detergent or shampoo or the like
  • a corresponding method according to the invention for providing (a) hair or (b) textile fibers with a vanilla, carnation and / or leathery fragrance comprises the following steps:
  • a corresponding method according to the invention for providing (a) hair or (b) textile fibers with a fruity, fresh and / or sweet smell comprises the following steps:
  • fragrance mixture comprising 2-methoxymethylphenol and one or more further fragrances, which convey one, several or all of the (olfactory) notes fresh, fruity and / or sweet, the amount at
  • 2-methoxymethylphenol is sufficient to modify and / or enhance (to boost) one or more of these notes
  • a surfactant-containing mixture in particular a solution which comprises: (a) water, (b) 2-methoxymethylphenol (for example, for example), is particularly suitable for the uses according to the invention or the corresponding processes which relate to the treatment of hair or textile fibers. in the form of a fragrance combination according to the invention) and (c) one or more surfactants, the concentration of 2-methoxymethylphenol in the solution being in the range from 10 ⁇ 7-10 ⁇ 1 % by weight.
  • Other fragrances (as part of a fragrance composition according to the invention, in particular one with a vanilla, carnation, leathery, fresh, fruity and / or sweet note) and / or other conventional additives may be present.
  • Preferred products according to the invention are (a) perfume oil mixtures (as an example for fragrance compositions according to the invention) for formulations containing surfactants, such as e.g. Cleaning agents, detergents, fabric softeners and personal care products and (b) the corresponding surfactant-containing formulations themselves.
  • surfactants such as e.g. Cleaning agents, detergents, fabric softeners and personal care products
  • the preferred surfactant-containing formulations which can be used in the context of the present invention generally comprise, in addition to the fragrance compositions according to the invention, substances from the class of anionic surfactants, such as carboxylates , Sulfates, sulfonates and phosphates, the cationic surfactants such as quaternary ammonium salts, the amphoteric surfactants such as betaines, and the nonionic surfactants such as ethoxylates and propoxylates.
  • anionic surfactants such as carboxylates , Sulfates, sulfonates and phosphates
  • the cationic surfactants such as quaternary ammonium salts
  • amphoteric surfactants such as betaines
  • nonionic surfactants such as ethoxylates and propoxylates.
  • the sulfates and sulfonates are preferred among the anionic surfactants.
  • the sulfates those having 12 to 18 carbon atoms and a degree of ethoxylation of 1 to a maximum of 5 are preferred.
  • Sodium lauryl ether sulfate is particularly preferred, preferably with an average degree of ethoxylation of 2 to 4.
  • the linear sodium alkylbenzenesulfonates with an average of about 12 carbon atoms in the alkyl chain are particularly preferred, these consisting of homologous residues with 10 to 14 carbon atoms (“dodecylbenzenesulfonate”).
  • the ethoxylated fatty alcohols which are obtained by ethoxylating alcohols with 12 to 18 carbon atoms (fatty alcohol ethoxylates with 12 to 18 C atoms) are preferred.
  • the degree of ethoxylation can vary within wide limits, but products with an average degree of ethoxylation of 5 to 10, in particular 7 moles of added ethylene oxide per mole of fatty alcohol are particularly preferred.
  • betaines those of the acid amide type with the structure listed are particularly preferred.
  • a corresponding surfactant formulation according to the invention (as an example of an article according to the invention) comprises 2-methoxymethylphenol and one or more surfactants which are selected from the group consisting of:
  • Linear alkylbenzenesulfonates (especially those mentioned above, such as the linear sodium alkylbenzenesulfonates),
  • Fatty alcohol ethoxylates with 12-18 C atoms (in particular those mentioned above, i.e. for example those with the degree of ethoxylation designated above as preferred),
  • Lauryl ether sulfates in particular those mentioned above, for example the sodium lauryl ether sulfate mentioned above
  • Betaines in particular those mentioned above, for example betaines of the acid amide type with the structure listed above.
  • Linear alkylbenzenesulfonates and fatty alcohol ethoxylates with 12-18 C atoms are preferably used next to one another, in particular in detergent powders.
  • lauryl ether sulfates in particular the above-mentioned sodium lauryl ether sulfate
  • betaines in particular betaines of the acid amide type with the structure listed above
  • concentration of the surface-active substances in the surfactant formulations according to the invention is generally not critical. Preferred concentrations depend on the type of surfactant and the particular application. For example, they can be less than 1% by weight in special bleaching products, but more than 99% by weight in soaps or washing powder. For certain fields of application, certain combinations and concentrations are preferred in surfactant formulations according to the invention.
  • Mixtures according to the invention are preferred in which the proportion of linear alkylbenzenesulfonates in the range from 7 to 10% by weight and / or the proportion of fatty alcohol ethoxylates with 12-18 C atoms in the range from 3 to 6% by weight is based on the total mass of the mixture.
  • Mixtures according to the invention (formulations for mild detergents, shampoos and shower gels) are also preferred in which the proportion of sodium lauryl ether sulfate is in the range from 7 to 13% by weight and / or the proportion of betaine (in particular betaine of the acid amide type with the structure listed above) Range of 1 - 3 wt .-%, based in each case on the total mass of the mixture.
  • 2-methoxymethylphenol is characterized by its fixing properties.
  • a fixator increases the adhesive strength of other fragrances, whether by lowering their vapor pressure or enhancing their odor (e.g. lowering the threshold value).
  • the invention therefore also relates, as already mentioned, to the use of 2-methoxymethylphenol or a fragrance mixture comprising 2-methoxymethylphenol (as characterized above) as a fixator.
  • 2-Methoxymethylphenol is preferably prepared using one of the etherification methods described above, starting from salicyl alcohol.
  • 2-methoxymethylphenol was produced, for example, from salicylaldehyde by reduction with sodium borohydride and subsequent etherification of the salicyl alcohol formed with methanol in the presence of sulfuric acid (see Example 1, below):
  • 2-methoxymethylphenol is particularly suitable for use in fragrance and flavoring compositions.
  • the compound can be used in numerous products in combination with a large number of other fragrance or aroma substances.
  • the compound can be combined particularly advantageously with other odoriferous or aromatic substances in different, different proportions to form novel odoriferous or aromatic substance compositions.
  • 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; Copaivabalsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts absolute; Oakmoss absolute; Ele
  • fragrances from the group of hydrocarbons such as 3-carene; alpha-pinene; beta-pinene; alpha terpinene; gamma terpinene; p-cymene; Bisabolene; Camphene; Caryophyllene; Cedren; Farnese; Lime; Longifolene; Myrcene; Ocimen; Valencene; (E 1 Z) -1, 3, 5-undecatriene; Styrene; Diphenylmethane; aliphatic alcohols such as 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-o
  • Methyl 2-noninate Allyl-2-isoamyloxyacetate; Methyl 3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate; the acyclic terpene alcohols such as B.
  • 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; 2-ethyl-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-trimethylcyclohexy
  • Trimethylcyclohexyl) hexan-3-ol Trimethylcyclohexyl) hexan-3-ol; cyclic and cycloaliphatic ethers such as e.g. Cineol; Cedryl methyl ether; Cyclododecyl methyl ether; 1, 1-dimethoxycyclododecane; (Ethoxymethoxy) cyclododecane; alpha-cedrenepoxide; 3a, 6, 6,9a-
  • 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; S-methyl- ⁇ -cyclopentadecenone; 3-
  • Methylcyclopentadecanone 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1,3,3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; ⁇ -cycloheptadecen-i-one; Cyclopentadecanone; Cyclohexadecanone; cycloaliphatic aldehydes such as e.g.
  • Pentylcyclohexyl acetate 3,3,5-trimethylcyclohexyl acetate; Decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-ylacetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthylacetate; 4,7-methano
  • the amount of 2-methoxymethylphenol used is preferably 0.0001 to 90% by weight, preferably 0.01 to 70% by weight and particularly preferably 0.1 to 50% by weight, based on the Total amount of the fragrance or flavoring composition.
  • Fragrance or flavoring compositions which contain 2-methoxymethylphenol can be used in liquid form, undiluted or diluted with a solvent for perfuming or aromatizing. Suitable solvents for this are e.g.
  • Ethanol isopropanol, diethylene glycol monoethyleter, glycerin, propylene glycol, 1, 2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, vegetable oils etc.
  • Ingredients that can be combined with 2-methoxymethylphenol include:
  • Preservatives Preservatives, abrasives, anti-acne agents, anti-aging agents, anti-bacterial agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritant agents, anti-irritant agents, antimicrobial agents, antioxidants, astringents, antiperspirant agents, antiseptic agents, antistatic agents , Buffers, carrier materials, chelating agents, cell stimulants, cleaning agents, care agents, depilatory agents, surface-active substances, deodorising agents, antiperspirants, softening agents, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, Foaming agents, foam stabilizers, substances to prevent foaming, foam boosters, fungicides, gelling agents, gelling agents, hair care products, hair shaping agents, hair straightening agents, moisturizing agents, moisturizing substances, moisturizing substances, bleaching agents, strengthening agents, stain-removing agents, optically brightening agents, imprinting agents
  • fragrance or flavoring compositions according to the invention which contain 2-methoxymethylphenol can be adsorbed on a carrier which ensures both a fine distribution of the fragrance or flavoring substances in the product and a controlled release during use.
  • a carrier which ensures both a fine distribution of the fragrance or flavoring substances 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, cellulose-based substances, sugars, dextrins (eg maltodextrin) or plastics such as PVC, polyvinyl acetates or polyurethanes.
  • the combination of composition and carrier according to the invention represents an exemplary article according to the invention.
  • Fragrance or flavoring compositions which contain 2-methoxymethylphenol can also be microencapsulated, spray-dried, as inclusion complexes or present as extrusion products (ie products according to the invention) and in this form, for. B. a product to be perfumed or flavored.
  • compositions 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.
  • 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 resulting products in turn represent products according to the invention.
  • the microencapsulation of the fragrance or flavoring compositions according to the invention to products according to the invention can be carried out, 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 fragrance or flavoring composition can be produced, for example, by spray drying an emulsion or dispersion containing the fragrance or flavoring composition, and modified starches, proteins, dextrin and vegetable gums can be used as carriers.
  • Inclusion complexes can e.g. by adding dispersions of the fragrance or flavoring composition and cyclodextrins or urea derivatives in a suitable solvent, e.g. Water.
  • Extrusion products can be made by fusing the fragrance or flavoring compositions with a suitable wax-like substance and by extrusion with subsequent solidification, if appropriate in a suitable solvent, e.g. Isopropanol can be obtained.
  • 2-methoxymethylphenol and fragrance compositions which contain 2-methoxymethylphenol can be used in concentrated form, in solutions or in the modified form described above for the production of perfumed products according to the invention, such as, 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-shaped carpet cleaners, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents such as bleach, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants and air fresheners applied in a liquid, gel-like or aerosol-based form on aerosol sprays and polishes such as furniture polishes,
  • the 2-methoxymethylphenol to be used according to the invention can be incorporated into flavored or flavored products, in particular preparations serving for nutrition, oral care or pleasure.
  • Preparations serving nutrition or pleasure are e.g. baked goods (e.g. bread, dry biscuits, cakes, other pastries), confectionery (e.g. chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (e.g. Coffee, tea, wine, wine-based drinks, beer, beer-based drinks, liqueurs, schnapps, brandies, fruit-containing lemonades, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juices juice preparations), instant drinks (e.g.
  • instant cocoa drinks, instant tea drinks, instant coffee drinks meat products (e.g. ham, fresh sausage or raw sausage preparations, seasoned or marinated fresh or pickled meat products), eggs or egg products (dry egg, protein, egg yolk) , Cereal products (e.g. breakfast cereals, granola bars, pre-cooked ready-rice products), dairy products (e.g. milk drinks, milk ice cream, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dry milk powder, whey, butter, buttermilk, partially or completely hydrolyzed milk protein-containing products) , Products made from soy protein or other soybean fractions (e.g.
  • soy milk and products made from it preparations containing soy lecithin, fermented products such as tofu or tempe or products made from it, soy sauces), fruit preparations (e.g. jams, fruit ice cream, fruit sauces, fruit fillings), vegetable preparations (e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked Vegetables, pickled vegetables, boiled vegetables), snacks (e.g. baked or fried potato chips or potato dough products, bread dough products, extrudates based on corn or peanuts), products based on fat and oil or emulsions thereof (e.g. mayonnaise, tartar sauce, dressings, seasoning preparations) , other ready meals and soups (e.g.
  • these preparations are preparations according to the invention (as an example of products according to the invention).
  • Preparations according to the invention can, for. B. as a semi-finished product or as a seasoning mix. Preparations according to the invention can serve, in particular, as semi-finished goods for the production of further preparations serving for nutrition or pleasure, in particular in spray-dried form. Preparations according to the invention can also be in the form of capsules, tablets (non-coated and coated tablets, for example enteric coatings), dragées, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsifiers. onen, as powder, as solutions, as pastes or as other swallowable or chewable preparations as food supplements.
  • Preparations according to the invention used for oral care are, in particular, oral and / or dental care products such as toothpastes, tooth gels, tooth powder, mouthwashes, chewing gums and other oral care products.
  • compositions according to the invention can be used in amounts of 5 to 99.999999% by weight, preferably 10 to 80% by weight, based on the Total weight of the preparation.
  • preparations can contain water in an amount of up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
  • the preparations according to the invention (as examples of products according to the invention) containing 2-methoxymethylphenol are prepared by using the 2-methoxymethylphenol as a substance, as a solution (for example in ethanol, water or 1,2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (e.g. maltodextrin, starch, silica gel), other flavors or flavorings and, if necessary, other auxiliaries and / or stabilizers (e.g. natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic) in a diet , oral care or basic preparation for pleasure.
  • a solid or liquid carrier e.g. maltodextrin, starch, silica gel
  • other auxiliaries and / or stabilizers e.g. natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic
  • Preparations according to the invention which are present as a solution and / or
  • the spray-dried solid preparations according to the invention are particularly well suited as semi-finished goods for the production of further preparations according to the invention.
  • the spray-dried solid preparations according to the invention preferably contain 50 to 95% by weight of carriers, in particular maltodextrin and / or starch, 5 to Contain 40% auxiliaries, preferably natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic.
  • the 2-methoxymethylphenol according to the invention and optionally other constituents of the preparation according to the invention are initially prepared in emulsions, in liposomes, e.g. starting from phosphatidylcholine, in microspheres, in nanospheres or also in capsules, granules or extrudates from a matrix suitable for foodstuffs and luxury foods, e.g. from starch, starch derivatives (e.g. modified starch), cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g.
  • dextrin alginate, curdlan, carageenan, chitin, chitosan, pullulan
  • natural fats natural waxes (e.g. beeswax, carnauba wax) Proteins, e.g. Gelatin or other natural products (e.g. shellac) incorporated.
  • the products can be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating (coating) or other suitable encapsulation processes and, if appropriate, a suitable combination of the aforementioned processes.
  • the 2-methoxymethylphenol is first complexed with one or more suitable complexing agents, for example with cyclodextrins or cyclodextrin derivatives, preferably ⁇ - or ⁇ -cyclodextrin, and used in this complexed form.
  • suitable complexing agents for example with cyclodextrins or cyclodextrin derivatives, preferably ⁇ - or ⁇ -cyclodextrin, and used in this complexed form.
  • a preparation according to the invention is particularly preferred in which the matrix is selected such that 2-methoxymethylphenol is released from the matrix with a delay, so that a long-lasting effect is achieved.
  • a fat, wax, polysaccharide or protein matrix is particularly preferred.
  • the usual constituents, auxiliaries and additives for foodstuffs or luxury foods for example water, mixtures of fresh or processed vegetable or animal raw materials or raw materials (for example raw materials) can be used as further constituents for preparations according to the invention which are used for nutrition or pleasure , roasted, dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetables or fruit juices or pastes or their mixtures), digestible or non-digestible carbohydrates (e.g. sucrose, maltose, fructose, Glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose), sugar alcohols (e.g.
  • sorbitol, erythritol natural or hardened fats (e.g. tallow, lard, palm fat, coconut fat, hardened vegetable fat), oils (e.g. sunflower oil, peanut oil, Corn oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or their salts (eg potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (eg gamma-aminobutyric acid, taurine), peptides (eg glutahthione), native or processed proteins (eg gelatin), enzymes (eg peptidases), nucleic acids, nucleotides, taste corrections for unpleasant taste impressions, further taste modulators for further, generally not unpleasant taste impressions, other taste-modulating substances (e.g.
  • inositol phosphate nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid
  • emulsifiers e.g. lecithins, diacylglycerols, gum arabic
  • stabilizers e.g. caramelizing agents Alginate
  • preservatives e.g. benzoic acid, sorbic acid
  • antioxidants e.g. tocopherol, ascorbic acid
  • chelators e.g. citric acid
  • organic or inorganic acidulants e.g. malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid
  • bitter substances e.g.
  • quinine quinine, caffeine) , Limonin, Amarogentin, Humolone, Lupolone, Catechine, Tannins), mineral salts (eg sodium chloride, potassium chloride, magnesium chloride, sodium phosphate), substances that prevent enzymatic browning (eg sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or color pigments (e.g. carotenoids, flavonoids, anthoc yane, chlorophyll and their derivatives), spices, trigeminally active substances or plant extracts, containing such trigeminally active substances, synthetic, natural or nature-identical flavorings or fragrances and odor correctors.
  • mineral salts eg sodium chloride, potassium chloride, magnesium chloride, sodium phosphate
  • substances that prevent enzymatic browning eg sulfite, ascorbic acid
  • essential oils e.g sulfite, ascorbic acid
  • plant extracts natural or synthetic dyes or color pigment
  • Dental care products (which are used as the basis for oral care preparations) and which contain 2-methoxymethylphenol generally comprise an abrasive system (Grinding or polishing agents), such as, for example, silicas, calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxylapatites, surface-active substances such as, for example, sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine, humectants such as, for example, glycerol and / or sorbitol, thickeners, such as carboxymethyl cellulose, polyethylene glycols, carrageenan and / or Laponite ® , sweeteners such as saccharin, taste corrections for unpleasant taste impressions, taste corrections for other, usually not unpleasant taste impressions, taste-modulating substances (eg inositol phosphate, nucleotides such as guanosine monophone) Substances such as sodium glutamate or
  • Diisopropylpropionic acid methylamide Diisopropylpropionic acid methylamide
  • cilin and cilin derivatives stabilizers and active ingredients, such as e.g. Sodium fluoride, sodium monofluorophosphate, Zinndifluo- chloride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures niumchlorid various pyrophosphates, triclosan, Cetylpyridi- ruchskorrigentien, aluminum lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavors and / or sodium bicarbonate or overall .
  • active ingredients such as e.g. Sodium fluoride, sodium monofluorophosphate, Zinndifluo- chloride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyr
  • Chewing gums (as another example of preparations used for oral care) which contain 2-methoxymethylphenol generally comprise a chewing gum base, ie a chewing gum which becomes plastic when chewed, sugars of various types, sugar substitutes, other sweet-tasting substances, sugar alcohols, taste corrections for unpleasant taste impressions, other taste modulators for other, usually not unpleasant, taste impressions, taste-modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), moisturizers, thickeners, emulsifiers, flavors and stabilizers or odors.
  • a chewing gum base ie a chewing gum which becomes plastic when chewed
  • sugars of various types, sugar substitutes, other sweet-tasting substances e.g., a sugar substitutes, other sweet-tasting substances, sugar alcohols, taste corrections for unpleasant taste
  • the preparations according to the invention can preferably also contain an (additional) aroma composition in order to round off and refine the taste and / or smell of the preparation.
  • Suitable (additional) aroma compositions contain, for example, synthetic, natural or nature-identical aromas, fragrances and flavors as well as suitable auxiliaries and carriers.
  • DPG dipropylene glycol
  • Table 3 shows some selected sensory data that illustrate the sensory potential of 2-methoxymethylphenol. Isobutylquinoline of the following formula was used for comparison:
  • the comparative substance isobutylquinoline was not selected here because of its own smell, but rather because of its property as a "booster” (cf. Insofar Arctander, in Perfume and Flavor Chemicals, as quoted above, “... the effect is more that of a general "lift” than actually an odor contribution, and the quinoline odor should not be part of the fragrance picture, but should appear with an undetectable note of radiation and strength. ").
  • Table 4 shows the stability of 2-methoxymethylphenol in different (surfactant-containing) products based on the analytical recovery rates.
  • 2-methoxymethylphenol was provided as a 50% by weight solution in diethyl phthalate, which was incorporated in a dosage of 0.2% by weight into a shampoo base composition of the following formulation: Sodium lauryl ether sulfate 12%
  • Peach fragrance mixture comprising gamma undecalactone 0.5%
  • the pH of the shampoo base was around 6. From this, 100 ml of a 20% by weight aqueous shampoo solution were produced. In this shampoo solution, 2 strands of hair were washed together for 2 minutes and then rinsed under running, lukewarm water for 20 seconds. One strand of hair was wrapped wet in aluminum foil and the second strand of hair was dried with a hair dryer. Both strands of hair were assessed in terms of smell by a panel. Both strands of hair showed a fresh, peach-fruity and sweet smell, whereby the overall impression was radiant, rounded, natural and harmonious.
  • the perfume oil composition from Example 2 (after the addition of 2-methoxymethylphenol) was incorporated in a dosage of 0.5% by weight into a fabric softener base of the following composition: Quaternary ammonium methosulfate (ester quat), approx. 90% 5.5% (e.g. Rewoquat WE 18, Witco Surfactants GmbH)
  • the pH of the fabric softener base was in the range 2 - 3.
  • Two cloths were rinsed with 370 g of a 1% aqueous fabric softener solution in a Linetest machine in the fabric softener program for 30 minutes at 20 ° C.
  • the rags were wrung out and then flung for 20 seconds.
  • a rag was welded wet and one hung up to dry. Subsequently, both cloths were assessed for odor by a panel.
  • Both rags showed a fresh, raspberry-fruity and vanilla-sweet smell with weak leathery-clove-like aspects, whereby the overall impression was radiant, rounded, natural and harmonious.

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Abstract

A description is given of the use of 2-methoxymethylphenol as perfume or aroma substance having a vanilla-like, clove-like and/or leather-like note. In addition, a description is given of the use of 2-methoxymethylphenol as a booster for perfumes or aroma substances, in particular for those having fresh, fruity and/or sweet notes.

Description

2-Methoxymethylphenol als Riech- und Aromastoff  2-methoxymethylphenol as a fragrance and aroma
Die vorliegende Erfindung betrifft primär die Verwendung von 2- Methoxymethylphenol als Riech- oder Aromastoff mit einer vanilligen, nelkigen und/oder ledrigen Note. Die Erfindung betrifft zudem die Verwendung von 2- Methoxymethylphenol als Booster (Verstärker; Enhancer) für Riech- oder Aroma- stoffe, insbesondere für Riech- oder Aromastoffe mit frischen, fruchtigen und/oder süßen Noten. The present invention relates primarily to the use of 2-methoxymethylphenol as a fragrance or aroma substance with a vanilla, carnation and / or leathery note. The invention also relates to the use of 2-methoxymethylphenol as a booster (enhancer) for fragrance or flavoring substances, in particular for fragrance or flavoring substances with fresh, fruity and / or sweet notes.
Die Erfindung betrifft ferner bestimmte Verfahren zum Vermitteln, Modifizieren und/oder Verstärken (Boosten) eines Geruchs- oder Geschmacks mit einer, mehreren oder sämtlichen der Noten vanillig, nelkig und/oder ledrig sowie Ver- fahren zum Modizifieren und/oder Verstärken (Boosten) eines Geruchs und/oder Geschmacks mit einer, mehreren oder sämtlichen der Noten frisch, fruchtig und/oder süß. The invention further relates to certain methods for imparting, modifying and / or enhancing (boosting) an odor or taste with one, several or all of the notes vanilla, clove-like and / or leathery, and methods for modifying and / or enhancing (boosting) a smell and / or taste with one, several or all of the notes fresh, fruity and / or sweet.
Die Erfindung betrifft auch bestimmte Riech- oder Aromastoffkompositionen, dieThe invention also relates to certain fragrance or flavoring compositions which
2-Methoxymethylphenol umfassen sowie Verfahren zur Herstellung entspre- chender Riech- oder Aromastoffkompositionen. Die Erfindung betrifft auch ein Produkt umfassend eine erfindungsgemäße Riech- oder Aromastoffkomposition (zu bevorzugten Produkttypen siehe unten). 2-Methoxymethylphenol include and processes for the preparation of corresponding fragrance or flavoring compositions. The invention also relates to a Product comprising a fragrance or flavoring composition according to the invention (for preferred product types see below).
Die Erfindung betrifft zudem die Verwendung von 2-Methoxymethylphenol oder einer 2-Methoxymethylphenol enthaltenden Mischung als Mittel zum Versehen von (a) Haaren oder (b) textilen Fasern mit einem vanilligen, nelkigen und/oder ledrigen Duft sowie entsprechende Verfahren und (vorzugsweise tensidhaltige) Mischungen. The invention also relates to the use of 2-methoxymethylphenol or a mixture containing 2-methoxymethylphenol as an agent for providing (a) hair or (b) textile fibers with a vanilla, carnation and / or leathery fragrance and corresponding methods and (preferably surfactant-containing) Mixtures.
Die Erfindung betrifft zudem die Verwendung von 2-Methoxymethylphenol als Mittel zum Erhöhen der Substantivität und/oder Retention einer Riechstoffmi- schung und/oder als Fixateur und die Verwendung von 2-Methoxymethylphenol als Mittel zum Erhöhen des über einer tensidhaltigen wässrigen Lösung wahrgenommenen Geruches anderer Riechstoffe. The invention also relates to the use of 2-methoxymethylphenol as an agent for increasing the substantivity and / or retention of an odorant mixture and / or as a fixator and the use of 2-methoxymethylphenol as an agent for increasing the odor of other odorants perceived via a surfactant-containing aqueous solution .
Die Erfindung betrifft auch Verfahren zum Versehen von (a) Haaren oder (b) textilen Fasern mit einem fruchtigen, frischen und/oder süßen Geruch. Schließlich betrifft die Erfindung auch Produkte, die 2-Methoxymethylphenol und daneben z. B. weitere Riechstoffe und/oder Tenside umfassen. The invention also relates to methods for providing (a) hair or (b) textile fibers with a fruity, fresh and / or sweet smell. Finally, the invention also relates to products containing 2-methoxymethylphenol and in addition, for. B. include other fragrances and / or surfactants.
Trotz einer Vielzahl bereits vorhandener Riechstoffe besteht in der Parfümindustrie auch weiterhin ein genereller Bedarf an neuen Riechstoffen, die über Ihre primären, nämlich geruchlichen Eigenschaften hinaus zusätzliche positive Se- kundäreigenschaften besitzen, wie z.B. eine höhere Stabilität unter bestimmten Anwendungsbedingungen, eine höhere Ausgiebigkeit, ein besseres Haftungsvermögen, eine größere Ausstrahlungskraft oder aber auch bessere dermatologische und toxikologische Eigenschaften gegenüber vergleichbaren Riechstoffen, wie z.B. eine gute biologische Abbaubarkeit. Gerade in der jüngsten Vergangenheit wurden bezüglich der zuletzt genannten Eigenschaften zunehmend Bedenken gegenüber einigen häufig eingesetzten Riechstoffe geäußert. Es ist zu erwarten, dass deren Einsatz zukünftig limitiert wird oder auf den Einsatz gänzlich verzichtet werden muss. Es besteht daher in der Parfümindustrie grundsätzlich ein Bedarf an weiteren Riechstoffen, die sich zur Herstellung von Riechstoffkompositionen oder parfümierten Artikeln eignen. Insbesondere besteht ein Bedarf an Riechstoffen, die durch die oben erwähnten technischen Eigenschaften wie Stärke oder Ausgie- bigkeit zu einem erhöhten Nutzen von Parfümölen führen. Despite a large number of existing fragrances, there is still a general need in the perfume industry for new fragrances which, in addition to their primary, namely odor properties, have additional positive secondary properties, such as, for example, greater stability under certain application conditions, higher yield, better quality Adhesion, a greater charisma or better dermatological and toxicological properties compared to comparable fragrances, such as good biodegradability. Especially in the recent past, concerns about some of the commonly used fragrances have been raised regarding the latter properties. It is to be expected that their use will be limited in the future or that the use will have to be dispensed with entirely. There is therefore basically a need in the perfume industry for further fragrances which are suitable for producing fragrance compositions or perfumed articles. In particular, there is a need for odoriferous substances which, due to the technical properties mentioned above, such as strength or yield, lead to an increased use of perfume oils.
Die vorliegende Erfindung betrifft gemäß einem primären Aspekt die Verwendung von 2-Methoxymethylphenol als Riech- oder Aromastoff mit einer vanilligen, nelkigen und/oder ledrigen Note. According to a primary aspect, the present invention relates to the use of 2-methoxymethylphenol as a fragrance or aroma substance with a vanilla, carnation and / or leathery note.
Ein weiterer Aspekt der vorliegenden Erfindung betrifft die Verwendung von 2- Methoxymethylphenol als Booster für Riech- oder Aromastoffe, insbesondere für Riech- oder Aromastoffe mit frischen, fruchtigen und/oder süßen Noten. Als „Booster" (Enhancer) verstärkt 2-Methoxymethylphenol die Geruchs- oder Geschmacksnoten von Riech- oder Aromastoffen, insbesondere frische, fruchtige und/oder süße Noten. Besonders ausgeprägt ist der sogenannte„Boost-Effekt" in Parfümölen, insbesondere Parfümölen mit fruchtigen, frischen und/oder süßen Noten. Another aspect of the present invention relates to the use of 2-methoxymethylphenol as a booster for fragrance or flavoring substances, in particular for fragrance or flavoring substances with fresh, fruity and / or sweet notes. As a "booster" (enhancer), 2-methoxymethylphenol enhances the smell or taste of odoriferous or aromatic substances, especially fresh, fruity and / or sweet notes. The so-called "boost effect" is particularly pronounced in perfume oils, especially perfume oils with fruity, fresh and / or sweet notes.
Die Strukturformel von 2-Methoxymethylphenol ist nachfolgend wiedergegeben:
Figure imgf000004_0001
The structural formula of 2-methoxymethylphenol is shown below:
Figure imgf000004_0001
Die Verbindung ist aus der Literatur bekannt. The connection is known from the literature.
So wird z.B. in J. Org. Chem. 1999, 64, 3012-3018 die Synthese von o- Methoxymethylphenol aus o-Hydroxybenzylalkohol (Salicylalkohol) und Methanol bei relativ niedriger Temperatur (424 K) beschrieben. For example, in J. Org. Chem. 1999, 64, 3012-3018 describes the synthesis of o-methoxymethylphenol from o-hydroxybenzyl alcohol (salicyl alcohol) and methanol at a relatively low temperature (424 K).
In Chem. Pharm. Bull. 2002, 50(3), 380-383 wird eine Veretherung mittels Triflu- ormethansulfonsäuresalzen der seltenen Erden beschrieben. - A - Chem. Pharm. Bull. 2002, 50 (3), 380-383 describes etherification using trifluoromethanesulfonic acid salts of the rare earths. - A -
In Acta Chem. Scand. 1999, 53, 258-262 erfolgt die Darstellung als Nebenprodukt bei der neuartigen ortho-Formylierung von Phenolen mittels Magnesiumchlorid und Triethylamine. In Acta Chem. Scand. 1999, 53, 258-262 is shown as a by-product in the novel ortho-formylation of phenols using magnesium chloride and triethylamine.
Die geruchlichen Eigenschaften von 2-Methoxymethylphenol (2-Hydroxy-benzyl- methyläther) wurden bis jetzt einmal beschrieben und zwar in der Zeitschrift „Riechstoffe, Aromen, Körperpflegemittel" 1964, 15(11), 407-9. Der Geruch wird als "an Guaiacol erinnernd" beschrieben. Es wurden keine Beispiele für die Effekte von 2-Methoxymethylphenol in Parfümölen angegeben. S. Arctander beschreibt Guaiacol in Perfume and Flavor Chemicals, Vol. I und II, Montclair, N. J., 1969, Selbstverlag, als Substanz mit starker rauchähnlicher, medizinischer Note, die süßer ist als diejenige des Phenols. The olfactory properties of 2-methoxymethylphenol (2-hydroxy-benzyl-methyl ether) have so far been described once, namely in the journal "Fragrances, Aromas, Personal Care Products" 1964, 15 (11), 407-9. The smell is referred to as " Guaiacol reminiscent ". No examples of the effects of 2-methoxymethylphenol in perfume oils were given. S. Arctander describes Guaiacol in Perfume and Flavor Chemicals, Vol. I and II, Montclair, NJ, 1969, self-published, as a substance with a strong smoke-like , medical grade that is sweeter than that of phenol.
Die Geruchsbeschreibung "an Guaiacol erinnernd" ist somit weder vollständig noch akkurat, wenn nicht gar völlig falsch. In eigenen Untersuchungen zeigte sich nämlich, dass das erfindungsgemäß einzusetzende 2-Methoxymethylphenol einen starken vanilligen, nelkigen und ledrigen Geruch aufweist. The description of the smell "reminiscent of Guaiacol" is therefore neither complete nor accurate, if not completely wrong. Our own investigations showed that the 2-methoxymethylphenol to be used according to the invention has a strong vanilla, carnation and leathery odor.
Zwei wichtige Aspekte der vorliegenden Erfindung, welche bevorzugte Verwendungen von 2-Methoxymethylphenol betreffen, wurden bereits vorstehend angegeben; weitere Aspekte der vorliegenden Erfindung ergeben sich insbesondere aus den beigefügten Patentansprüchen, aber auch aus der vorliegenden Be- Schreibung inklusive der Beispiele. Two important aspects of the present invention, which relate to preferred uses of 2-methoxymethylphenol, have already been stated above; further aspects of the present invention result in particular from the attached patent claims, but also from the present description including the examples.
Die Tatsache, dass 2-Methoxymethylphenol in Übereinstimmung mit dem ersten Aspekt der vorliegenden Erfindung einen ausdrucksstarken Geruch nach Vanille, Nelke und Leder aufweist, ist überraschend, da es sich strukturell von bekannten Substanzen mit ähnlichem Geruch unterscheidet. Üblicherweise führt ein Wech- sei von Substitutionsmustern an aromatischen Ringen auch bei ansonsten strukturell ähnlichen Verbindungen zu deutlich unterschiedlichen olfaktorischen Eigenschaften. Die nachfolgende Tabelle 1 zeigt exemplarisch ausgewählte Verbindungen, deren geruchliche Eigenschaften mit nelkig, vanillig oder ledrig beschrieben sind (K. Bauer, D. Garbe und H. Surburg, Common Fragrance and Flavor Materials, 4rd. Ed., Wiley-VCH, Weinheim 2001 ): Tabelle 1 : The fact that 2-methoxymethylphenol in accordance with the first aspect of the present invention has an expressive smell of vanilla, clove and leather is surprising since it is structurally different from known substances with a similar smell. A change of substitution patterns on aromatic rings usually leads to significantly different olfactory properties even with otherwise structurally similar compounds. The following Table 1 shows examples of selected compounds whose olfactory properties are described with nelkig, vanilla or leathery (K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials, 4 approx. Ed., Wiley-VCH, Weinheim 2001): Table 1 :
Geruchsbe¬Odor
Name Struktur Name structure
schreibung  spelling
Eugenol nelkig
Figure imgf000006_0001
Eugenol carnation
Figure imgf000006_0001
Isoeugenol nelkig
Figure imgf000006_0002
Isoeugenol carnation
Figure imgf000006_0002
Vanillin vanillig, süß
Figure imgf000006_0003
Vanilla vanilla, sweet
Figure imgf000006_0003
p-tert.-Butylphenol ledrig
Figure imgf000006_0004
Es ist erstaunlich, dass 2-Methoxymethylphenol die sensorischen Eigenschaften aller oben genannten Verbindungen in sich vereint, während diese jeweils nur für eine Geruchsrichtung charakteristisch sind.
p-tert-butylphenol leathery
Figure imgf000006_0004
It is astonishing that 2-methoxymethylphenol combines the sensory properties of all the above-mentioned compounds, while these are only characteristic of one smell.
Wie oben bereits ausgeführt, wurde gemäß einem weiteren Aspekt der vorliegenden Erfindung gefunden, dass sich 2-Methoxymethylphenol hervorragend zum Verstärken (Boosten) eines Geruchs oder Geschmacks mit fruchtigen, frischen und/oder süßen Noten eignet. Diese Eigenschaft des 2- Methoxymethylphenol wird anhand eines Parfümöls mit fruchtiger Himbeernote in Beispiel 2 illustriert (siehe unten). In analogen Untersuchungen wurden besonders gute Ergebnisse erhalten, wenn 2-Methoxymethylphenol mit einer oder mehreren der in Tabelle 2 aufgeführten Verbindungen kombiniert wurde. As already stated above, according to a further aspect of the present invention, it was found that 2-methoxymethylphenol is outstandingly suitable for enhancing (boosting) an odor or taste with fruity, fresh and / or sweet notes. This property of 2-methoxymethylphenol is illustrated using a perfume oil with a fruity raspberry note in Example 2 (see below). In analogous tests, particularly good results were obtained when 2-methoxymethylphenol was combined with one or more of the compounds listed in Table 2.
Tabelle 2: Verbindungen mit fruchtiger, frischer und/oder süßer Note zur bevorzugten Kombination mit 2-Methoxymethylphenol Table 2: Compounds with a fruity, fresh and / or sweet note for the preferred combination with 2-methoxymethylphenol
Figure imgf000007_0001
Ethyl-3-methyl-3-
Figure imgf000007_0001
Ethyl-3-methyl-3-
Erdbeere strawberry
phenylglycidat phenyl glycidate
Figure imgf000008_0001
Figure imgf000008_0001
Buttersäureisoamylester Isamic acid butyrate
Banane  banana
(Isoamylbutyrat)  (Isoamyl butyrate)
Essigsäureisoamylester Isoacetic acid acetate
Banane  banana
(Isoamylacetat)  (Isoamyl acetate)
Essigsäure-n-butylester N-Butyl acetate
Apfel  Apple
(Butylacetat)  (Butyl acetate)
Buttersäureethylester Ethyl butyrate
Ananas  pineapple
(Ethylbutyrat)  (Ethyl butyrate)
3-Methyl- buttersäureethylester Blaubeeren 3-methyl-butyric acid ethyl blueberries
o (Ethylisovalerat)  o (ethyl isovalerate)
n-Hexansäureethylester n-Hexanoic acid ethyl ester
Ananas  pineapple
(Ethylcaproat)
Figure imgf000008_0002
Figure imgf000009_0001
Figure imgf000010_0001
(Ethyl caproat)
Figure imgf000008_0002
Figure imgf000009_0001
Figure imgf000010_0001
Vorstehend wurde erläutert, dass gemäß einem ersten Aspekt der vorliegenden Erfindung 2-Methoxymethylphenol als Riech- oder Aromastoff mit einer vanilligen, nelkigen und/oder ledrigen Note verwendet wird. Ein entsprechendes erfindungsgemäßes Verfahren zum Vermitteln, Modifizieren und/oder Verstärken (Boosten) eines Geruchs oder Geschmacks mit einer, mehreren oder sämtlichen der Noten vanillig, nelkig und/oder ledrig umfasst einen Schritt, in dem eine Menge 2-Methoxymethylphenol oder einer 2-Methoxymethylphenol umfassenden Riech- oder Aromastoffkomposition mit einem Erzeugnis in Kontakt gebracht oder gemischt wird. Das Erzeugnis kann dabei beispielsweise ein weiterer Riechoder Aromastoff oder eine Mischung weiterer Riech- oder Aromastoffe sein. It was explained above that according to a first aspect of the present invention, 2-methoxymethylphenol is used as a fragrance or aroma substance with a vanilla, carnation and / or leathery note. A corresponding method according to the invention for imparting, modifying and / or enhancing (boosting) an odor or taste with one, several or all of the notes vanilla, clove-like and / or leathery comprises a step in which a quantity of 2-methoxymethylphenol or a 2-methoxymethylphenol comprehensive fragrance or flavoring composition is brought into contact with a product or mixed. The product can be, for example, a further fragrance or flavoring substance or a mixture of other fragrance or flavoring substances.
Mit Blick auf einen zweiten Aspekt der vorliegenden Erfindung wurde bereits ausgeführt, dass 2-Methoxymethylphenol als Booster für Riech- oder Aromastof- fe verwendet werden kann. Ein entsprechendes Verfahren zum Modifizieren und/oder Verstärken (Boosten) eines Geruchs und/oder Geschmacks mit einer, mehreren oder sämtlichen der Noten frisch, fruchtig und/oder süß umfasst den folgenden Schritt: With regard to a second aspect of the present invention, it has already been stated that 2-methoxymethylphenol acts as a booster for odoriferous or flavoring substances. fe can be used. A corresponding method for modifying and / or enhancing (boosting) an odor and / or taste with one, several or all of the notes fresh, fruity and / or sweet comprises the following step:
- Vermischen eines oder mehrerer Riech- oder Aromastoffe mit einer, mehreren oder sämtlichen der Noten frisch, fruchtig und/oder süß, mit einer Menge an 2-Methoxymethylphenol, die ausreicht, den Geruchs- und/oder Geschmackseindruck des bzw. der Riech- oder Aromastoffe, die eine oder mehrere der Noten frisch, fruchtig und/oder süß verursachen, sensorisch zu modifizieren und/oder zu verstärken. - Mixing one or more fragrance or aroma substances with one, several or all of the notes fresh, fruity and / or sweet, with an amount of 2-methoxymethylphenol which is sufficient to give the odor and / or taste impression of the odorant or Aroma substances that cause one or more of the notes fresh, fruity and / or sweet to be modified by sensors and / or intensified.
In Mischungen mit anderen Riech- oder Aromastoffen vermag das erfindungsgemäß einzusetzende 2-Methoxymethylphenol bereits in geringen Dosierungen die Intensität der Riech- bzw. Aromastoffmischung zu verstärken und das Gesamtbild der Mischung geruchlich abzurunden sowie der Mischung mehr Aus- Strahlung, Glanz, Harmonie sowie Natürlichkeit zu verleihen. In mixtures with other fragrance or aroma substances, the 2-methoxymethylphenol to be used according to the invention is able to intensify the intensity of the fragrance or aroma substance mixture even in small doses and to round off the overall appearance of the mixture and to give the mixture more radiance, gloss, harmony and naturalness to lend.
Riech- oder Aromastoffkompositionen, die 2-Methoxymethylphenol und einen oder mehrere weitere Riech- oder Aromastoffe umfassen (insbesondere Riechoder Aromastoffe mit fruchtiger, frischer und/oder süßer Note) besitzen eine überraschende geruchliche Qualität. Die Erfindung betrifft auch entsprechende Riech- oder Aromastoffkompositionen, die 2-Methoxymethylphenol und einen oder mehrere weitere Riech- oder Aromastoffe umfassen. Es sind dabei zumindest drei unterschiedliche Typen von erfindungsgemäßen Riech- oder Aromastoffkompositionen voneinander unterscheidbar, wobei allerdings die Übergänge vom einen Typ zum anderen fließend sind. In Typ (i) einer erfindungsgemäßen Riech- oder Aromastoffkomposition reicht die Menge an 2-Methoxymethylphenol aus, eine, mehrere oder sämtliche der Noten vanillig, nelkig und/oder ledrig zu vermitteln. Dieser Kompositionstyp (i) liegt insbesondere dann vor, wenn keiner der weiteren Riech- oder Aromastoffe selbst eine, mehrere oder sämtliche der Noten vanillig, nelkig und/oder ledrig vermittelt, aber die Menge an 2-Methoxymethylphenol ausreicht, eine, mehrere oder sämtliche dieser Noten zu vermitteln. Fragrance or flavoring compositions which comprise 2-methoxymethylphenol and one or more further fragrance or flavoring substances (in particular fragrance or flavoring substances with a fruity, fresh and / or sweet note) have a surprising olfactory quality. The invention also relates to corresponding fragrance or flavoring compositions which comprise 2-methoxymethylphenol and one or more further fragrance or flavoring substances. At least three different types of fragrance or flavoring compositions according to the invention can be distinguished from one another, although the transitions from one type to the other are fluid. In type (i) of a fragrance or aroma composition according to the invention, the amount of 2-methoxymethylphenol is sufficient to impart one, more or all of the notes vanilla, clove-like and / or leathery. This type of composition (i) exists in particular when none of the other fragrance or aroma substances itself conveys one, several or all of the notes vanilla, carnation and / or leathery, but the amount of 2-methoxymethylphenol is sufficient to convey one, several or all of these notes.
In Typ (ii) einer erfindungsgemäßen Riech- oder Aromastoffkomposition vermitteln der oder die weiteren Riech- oder Aromastoffe eine, mehrere oder sämtliche der Noten vanillig, nelkig, ledrig, frisch, fruchtig und/oder süß und die Menge an 2-Methoxymethylphenol reicht aus, eine oder mehrere dieser Noten zu modifizieren und/oder zu verstärken (zu boosten). In type (ii) of a fragrance or flavoring composition according to the invention, the further fragrance or flavoring agent (s) impart one, several or all of the notes vanilla, clove-like, leathery, fresh, fruity and / or sweet and the amount of 2-methoxymethylphenol is sufficient, modify and / or reinforce (to boost) one or more of these notes.
Gemäß Typ (iii) einer erfindungsgemäßen Riech- oder Aromastoffkomposition reicht die Menge an 2-Methoxymethylphenol aus, der Riech- oder Aromastoff- komposition (Aus)Strahlung, Glanz, Abrundung, Natürlichkeit und/oder Harmonie zu verleihen. According to type (iii) of a fragrance or flavoring composition according to the invention, the amount of 2-methoxymethylphenol is sufficient to give the fragrance or flavoring composition (out) radiation, gloss, roundness, naturalness and / or harmony.
Besonders bevorzugt sind erfindungsgemäße Riech- oder Aromastoffkompositionen, die neben dem erfindungsgemäß einzusetzenden 2-Methoxymethylphenol einen oder mehrere weitere Riech- oder Aromastoffe enthalten, die ausgewählt sind aus der Gruppe bestehend aus: Particularly preferred are fragrance or flavoring compositions according to the invention which, in addition to the 2-methoxymethylphenol to be used according to the invention, contain one or more further fragrance or flavorings which are selected from the group consisting of:
2-Methyl-buttersäureethylester, 4-(p-Hydroxyphenyl)-2-butanon, Ethyl-3-methyl- 3-phenylglycidat, Buttersäureisoamylester, Essigsäureisoamylester, Essigsäure- n-butylester, Buttersäureethylester, 3-Methyl-buttersäureethylester, n- Hexansäureethylester, n-Hexansäureallylester, Ethyl-2-trans-4-cis-decadienoat, 1 ,1 -Dimethoxy-2,2,5-trimethyl-4-hexan, 2,6-Dimethyl-5-hepten-1-al, gamma- Undecalacton, gamma-Nonalacton, Vanillin, Ethylvanillin, Maltol, Ethylmaltol und deren Mischungen. Vergleiche insoweit Tabelle 2, oben.  2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl 3-methyl-3-phenylglycidate, butyric acid isamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis decadienoate, 1, 1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, gamma Undecalactone, gamma-nonalactone, vanillin, ethylvanillin, maltol, ethylmaltol and mixtures thereof. Compare Table 2 above.
Ganz besonders bevorzugt sind Kompositionen umfassend 2- Methoxymethylphenol und einen oder mehrere weitere Riech- oder Aromastoffe gewählt aus der Gruppe bestehend aus 2-Methyl-buttersäureethylester, 4-(p- Hydroxyphenyl)-2-butanon, Ethyl-3-methyl-3-phenylglycidat, Buttersäureisoamylester, Essigsäureisoamylester, Essigsäure-n-butylester, Buttersäureethylester, 3-Methyl-buttersäureethylester, n-Hexansäureethylester, n-Hexansäureallylester, Ethyl-2-trans-4-cis-decadienoat, 1 ,1-Dimethoxy-2,2,5-trimethyl-4-hexan, 2,6- Dimethyl-5-hepten-1-al, gamma-Undecalacton, und gamma-Nonalacton, d. h. die Verbindungen der Tabelle 2 mit Ausnahme von Vanillin, Ethylvanillin, Maltol und Ethylmaltol. 2-Methoxymethylphenol erzielt in Kombination mit diesen Verbindungen mit fruchtigen Geschmacksnoten die besten sensorischen Ergebnisse und Effekte. Insbesondere bevorzugt sind erfindungsgemäße Riech- oder Aromastoffkompositionen (insbesondere umfassend Verbindungen der Tabelle 2), die eine Menge an 2-Methoxymethylphenol im Bereich von 0,0001 bis 90 Gew.-%, vorzugsweise 0,01 bis 70 Gew.-% und besonders bevorzugt 0,1 bis 50 Gew.-%, umfassen, bezogen auf die Gesamtmenge der Riech- oder Aromastoffkomposition. Sofern 2-Methoxymethylphenol hauptsächlich eingesetzt wird, um einer Riechoder Aromastoffkomposition mehr (Aus)Strahlung, Glanz, Abrundung, Natürlichkeit und/oder Harmonie zu verleihen und/oder bestimmte Noten zu modifizieren bzw. zu verstärken, insbesondere Noten der Richtungen fruchtig, frisch und/oder süß, ist der Anteil an 2-Methoxymethylphenol vorzugsweise recht niedrig und vorzugsweise im Bereich von 0,01 bis 5 Gew.-%, bevorzugt im Bereich von 0,1 bis 2 Gew.-%, bezogen auf die Gesamtmenge der Riech- oder Aromastoffkomposition. Sofern innerhalb der bevorzugten Konzentrationsbereiche eine vergleichsweise niedrige Konzentration gewählt wird, kommt es in Abhängigkeit von den weiteren Komponenten der jeweiligen Komposition in manchen Fällen noch nicht zu der Vermittlung der oben angegebenen Eigengeruchs- oder - geschmacksnoten. Compositions comprising 2-methoxymethylphenol and one or more further odoriferous or aromatic substances selected from the group consisting of 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl-3-methyl-3- phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1, 1-dimethoxy-2,2 5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, gamma-undecalactone, and gamma-nonalactone, ie the Compounds in Table 2 with the exception of vanillin, ethylvanillin, maltol and ethylmaltol. In combination with these compounds with fruity flavors, 2-methoxymethylphenol achieves the best sensory results and effects. Particularly preferred are fragrance or flavoring compositions according to the invention (in particular comprising compounds of Table 2) which contain an amount of 2-methoxymethylphenol in the range from 0.0001 to 90% by weight, preferably 0.01 to 70% by weight and particularly preferred 0.1 to 50 wt .-%, based on the total amount of the fragrance or flavoring composition. If 2-methoxymethylphenol is mainly used to give a fragrance or aroma composition more radiation, shine, roundness, naturalness and / or harmony and / or to modify or reinforce certain notes, especially notes of the fruity, fresh and / or sweet, the proportion of 2-methoxymethylphenol is preferably quite low and preferably in the range from 0.01 to 5% by weight, preferably in the range from 0.1 to 2% by weight, based on the total amount of odoriferous or Flavor composition. If a comparatively low concentration is selected within the preferred concentration ranges, depending on the other components of the respective composition, the intrinsic odor or taste notes given above are not conveyed in some cases.
Erfindungsgemäße Riech- oder Aromastoffkompositionen werden vorzugsweise zur Herstellung parfümierter oder aromatisierter Produkte (Artikel) eingesetzt; zu bevorzugten parfümierten bzw. aromatisierten Produkten siehe unten. Die sensorischen Eigenschaften, stofflichen Eigenschaften (wie Löslichkeit in gängigen Lösungsmitteln und Kompatibilität mit gängigen weiteren Bestandteilen derartiger Produkte) sowie die toxikologische Unbedenklichkeit der erfindungsgemäß einzusetzenden Verbindung unterstreichen ihre besondere Eignung für die genannten Einsatzzwecke. Besonders bevorzugt sind erfindungsgemäße Riech- oder Aromastoffkompositionen, bei denen die Effekte der Typen (i), (ii) und (iii) nebeneinander und einander überlagernd auftreten. Ein Beispiel für eine derartige bevorzugte Riechstoffkomposition (Parfümkomposition) ist unten in Beispiel 2 gegeben. Ausgehend von einer Basiskomposition werden durch den Zusatz einer Menge an 2- Methoxymethylphenol (i) die Noten vanillig, nelkig und ledrig hinzugefügt (vermittelt), (ii) der Eindruck von Frische und Fruchtigkeit wird verstärkt und die Komposition wird (iii) insgesamt glänzender, abgerundeter und besitzt mehr Harmonie sowie Natürlichkeit. Durch Variation der Ausgangskomposition kann der Fach- mann zu einer Vielzahl weiterer Riechstoffkompositionen gelangen, in denen die Effekte der Typen (i), (ii) und (iii) nebeneinander auftreten. Fragrance or flavoring compositions according to the invention are preferably used for the production of perfumed or flavored products (articles); for preferred perfumed or flavored products see below. The sensory properties, material properties (such as solubility in common solvents and compatibility with other common constituents of such products) and the toxicological harmlessness of the compound to be used according to the invention underline their particular suitability for the purposes mentioned. Fragrance or flavoring compositions according to the invention are particularly preferred in which the effects of types (i), (ii) and (iii) occur side by side and overlapping one another. An example of such a preferred fragrance composition (perfume composition) is given in Example 2 below. Starting from a basic composition, the addition of a quantity of 2-methoxymethylphenol (i) adds (conveyed) the notes of vanilla, carnation and leathery, (ii) the impression of freshness and fruitiness is strengthened and (iii) the composition becomes overall shiny, more rounded and has more harmony and naturalness. By varying the starting composition, the expert can arrive at a large number of further fragrance compositions in which the effects of types (i), (ii) and (iii) occur side by side.
Eine erfindungsgemäße Riech- oder Aromastoffkomposition wird erfindungsgemäß hergestellt, indem 2-Methoxymethylphenol mit üblichen weiteren Bestandteilen einer Riech- oder Aromastoffkomposition vermischt wird, wobei das 2- Methoxymethylphenol in einer Menge eingesetzt wird, die ausreicht, um in der Riech- oder Aromastoffkomposition eine Geruchs- oder Geschmacksnote zu vermitteln, zu modifizieren und/oder zu verstärken. Das weiter unten angegebene Beispiel einer„fruchtig-vanilligen Himbeer"-Riechstoffkomposition demonstriert in anschaulicher Weise den olfaktorischen Effekt von 2-Methoxymethylphenol. In einem bevorzugten Verfahren zur Herstellung einer Riech- oder Aromastoffkomposition mit fruchtiger, frischer und/oder süßer Note umfassen die üblichen Bestandteile der Riech- oder Aromastoffkomposition Riech- oder Aromastoffe, die ausgewählt sind aus der bereits oben genannten Gruppe, die besteht aus: 2-Methyl-buttersäureethylester, 4-(p-Hydroxyphenyl)-2-butanon, Ethyl-3-methyl- 3-phenylglycidat, Buttersäureisoamylester, Essigsäureisoamylester, Essigsäure- n-butylester, Buttersäureethylester, 3-Methyl-buttersäureethylester, n- Hexansäureethylester, n-Hexansäureallylester, Ethyl-2-trans-4-cis-decadienoat, 1 ,1 -Dimethoxy-2,2,5-trimethyl-4-hexan, 2,6-Dimethyl-5-hepten-1-al, gamma- Undecalacton, gamma-Nonalacton, Vanillin, Ethylvanillin, Maltol, Ethylmaltol und deren Mischungen. Besonders bevorzugt sind hierbei wiederum die Verbindungen 2-Methyl- buttersäureethylester, 4-(p-Hydroxyphenyl)-2-butanon, Ethyl-3-methyl-3- phenylglycidat, Buttersäureisoamylester, Essigsäureisoamylester, Essigsäure-n- butylester, Buttersäureethylester, 3-Methyl-buttersäureethylester, n- Hexansäureethylester, n-Hexansäureallylester, Ethyl-2-trans-4-cis-decadienoat, 1 ,1 -Dimethoxy-2,2,5-trimethyl-4-hexan, 2,6-Dimethyl-5-hepten-1-al, gamma Undecalacton, gamma-Nonalacton und deren Mischungen. A fragrance or flavoring composition according to the invention is produced according to the invention by mixing 2-methoxymethylphenol with customary further constituents of a fragrance or flavoring composition, the 2-methoxymethylphenol being used in an amount sufficient to provide an odor in the fragrance or flavoring composition. or to convey, modify and / or reinforce taste. The example of a "fruity-vanilla raspberry" fragrance composition given below clearly demonstrates the olfactory effect of 2-methoxymethylphenol. In a preferred method for producing a fragrance or flavoring composition with a fruity, fresh and / or sweet note, the usual components are included the olfactory or aroma substance composition olfactory or aroma substances, which are selected from the group already mentioned above, which consists of: 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl-3-methyl-3- phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1, 1-dimethoxy-2,2-dimethoxy 5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, gamma undecalactone, gamma nonalactone, vanillin, ethyl vanillin, maltol, ethyl maltol and mixtures thereof. Again, the compounds 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl 3-methyl-3-phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl are particularly preferred -butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis-decadienoate, 1, 1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-heptene -1-al, gamma undecalactone, gamma-nonalactone and mixtures thereof.
Die Erfindung betrifft auch die Verwendung von 2-Methoxymethylphenol als Mittel zum Erhöhen der Substantivität und/oder Retention einer Riechstoffmi- schung (Riechstoffkomposition) und/oder als Fixateur. The invention also relates to the use of 2-methoxymethylphenol as an agent for increasing the substantivity and / or retention of a fragrance mixture (fragrance composition) and / or as a fixator.
2-Methoxymethylphenol bzw. 2-Methoxymethylphenol enthaltende Riechstoffmischungen (wie oben charakterisiert) zeichnen sich durch ein hohes Aufziehvermögen (Eigenhaftung auf einem Substrat) und eine hohe Substantivität (Fähigkeit, aus einer, meist wässrigen, Phase heraus auf ein Substrat aufzuziehen bzw. auch nach einem Wasch- oder Spülvorgang auf einem Substrat zu verbleiben) aus. Dieser Effekt zeigt sich insbesondere auf Substraten wie Haut, Haar und textilen Fasern (z.B. Wolle, Baumwolle, Leinen, synthetische Fasern). Fragrance mixtures containing 2-methoxymethylphenol or 2-methoxymethylphenol (as characterized above) are characterized by a high absorbency (self-adhesion on a substrate) and a high substantivity (ability to absorb from a, usually aqueous, phase onto a substrate or also after a washing or rinsing process to remain on a substrate). This effect is particularly evident on substrates such as skin, hair and textile fibers (e.g. wool, cotton, linen, synthetic fibers).
Besonders bevorzugte erfindungsgemäße parfümierte Produkte sind daher Waschmittel, Hygiene- oder Pflegeprodukte, insbesondere im Bereich der Kör- per- und Haarpflege, der Kosmetik und des Haushalts. Particularly preferred perfumed products according to the invention are therefore detergents, hygiene or care products, in particular in the field of body and hair care, cosmetics and the household.
Eine weitere wichtige einbindungstechnische Anforderung an Riechstoffe und Riechstoffmischungen insbesondere für tensidhaltige Produkte ist deren Substantivität gegenüber dem bzw. Retention am Substrat, insbesondere Haaren oder textilen Fasern. Die Begriffe "Substantivität" und "Retention" werden z.B. in EP 1 201 738 A1 ausführlich dargelegt, vgl. dort die Abschnitte [0004]-[0005]. Gesucht werden daher auch generell Riechstoffe mit hoher Substantivität und/oder Retention. Another important integration-related requirement for fragrances and fragrance mixtures, in particular for products containing surfactants, is their substantivity towards or retention on the substrate, in particular hair or textile fibers. The terms "substantivity" and "retention" are e.g. detailed in EP 1 201 738 A1, cf. there the sections [0004] - [0005]. Fragrance substances with high substantivity and / or retention are therefore also generally sought.
Diesen Erkenntnissen entsprechend betrifft der genannte weitere Aspekt derAccording to these findings, the further aspect of
Erfindung insbesondere die Verwendung von 2-Methoxymethylphenol als Mittel zum Erhöhen der Substantivität und/oder Retention einer Riechstoffmischung (insbesondere gegenüber bzw. auf Haaren bzw. textilen Fasern), vorzugsweise einer Riechstoffmischung mit fruchtiger, frischer und/oder süßer Note. Durch Zusatz von 2-Methoxymethylphenol zu einer vorgegebenen Riechstoffmischung nur geringer Substantivität und/oder Retention werden diese Eigenschaften in besonders vorteilhafter Weise verbessert. So lässt sich beispielsweise eine zwar fruchtig, frisch und/oder süß duftende, aber aufgrund nur mangelhafter Substantivität der enthaltenen Duftstoffe nicht zum Weitergeben eines fruchtigen, frischen und/oder süßen Geruchs an Wäsche (textile Fasern) oder Haare geeignete wässrige Waschlösung (bzw. ein entsprechendes Waschmittel oder Shampoo oder dergleichen) durch Zusatz von 2-Methoxymethylphenol in eine Lösung überführen, die einen fruchtigen, frischen und/oder süßen Geruch hervorragend weitergibt - und an den behandelten Substraten (Haare bzw. textile Fasern) haftet der fruchtige, frische und/oder süß Geruch lange an. Invention in particular the use of 2-methoxymethylphenol as an agent for increasing the substantivity and / or retention of a fragrance mixture (especially opposite or on hair or textile fibers), preferably a fragrance mixture with a fruity, fresh and / or sweet note. By adding 2-methoxymethylphenol to a given fragrance mixture with only low substantivity and / or retention, these properties are improved in a particularly advantageous manner. For example, a fruity, fresh and / or sweet-scented, but due to insufficient substantivity of the fragrances contained, not suitable for passing on a fruity, fresh and / or sweet smell to laundry (textile fibers) or hair, an aqueous washing solution (or a Corresponding detergent or shampoo or the like) by adding 2-methoxymethylphenol into a solution that excellently transmits a fruity, fresh and / or sweet smell - and the fruity, fresh and / adheres to the treated substrates (hair or textile fibers) or sweet smell for a long time.
Ein entsprechendes erfindungsgemäßes Verfahren zum Versehen von (a) Haa- ren oder (b) textilen Fasern mit einem vanilligen, nelkigen und/oder ledrigen Duft umfasst die folgenden Schritte: A corresponding method according to the invention for providing (a) hair or (b) textile fibers with a vanilla, carnation and / or leathery fragrance comprises the following steps:
Bereitstellen einer 2-Methoxymethylphenol enthaltenden Mischung, Applizieren der Mischung auf das Haar oder die textilen Fasern. Providing a mixture containing 2-methoxymethylphenol, applying the mixture to the hair or the textile fibers.
Ein entsprechendes erfindungsgemäßes Verfahren zum Versehen von (a) Haa- ren oder (b) textilen Fasern mit einem fruchtigen, frischen und/oder süßen Geruch umfasst die folgenden Schritte: A corresponding method according to the invention for providing (a) hair or (b) textile fibers with a fruity, fresh and / or sweet smell comprises the following steps:
Bereitstellen einer (erfindungsgemäßen) Riechstoffmischung (Riechstoffkomposition), umfassend 2-Methoxymethylphenol und einen oder mehrere weitere Riechstoffe, der bzw. die eine, mehrere oder sämtliche der (Ge- ruchs-)Noten frisch, fruchtig und/oder süß vermitteln, wobei die Menge anProviding a fragrance mixture (fragrance composition) according to the invention, comprising 2-methoxymethylphenol and one or more further fragrances, which convey one, several or all of the (olfactory) notes fresh, fruity and / or sweet, the amount at
2-Methoxymethylphenol ausreicht, eine oder mehrere dieser Noten zu modifizieren und/oder zu verstärken (zu boosten), 2-methoxymethylphenol is sufficient to modify and / or enhance (to boost) one or more of these notes,
Applizieren der Mischung auf das Haar oder die textilen Fasern. Für die erfindungsgemäßen Verwendungen bzw. die entsprechenden Verfahren, welche die Behandlung von Haaren oder textilen Fasern betreffen, besonders geeignet ist eine tensidhaltige Mischung, insbesondere eine Lösung, die umfasst: (a) Wasser, (b) 2-Methoxymethylphenol (z. B. in Form einer erfindungsgemäßen Riechstoffkombination) sowie (c) ein oder mehrere Tenside, wobei die Konzentration an 2-Methoxymethylphenol in der Lösung im Bereich von 10~7 - 10~1 Gew.- % liegt. Weitere Riechstoffe (als Bestandteil einer erfindungsgemäßen Riechstoffkomposition, insbesondere einer mit vanilliger, nelkiger, ledriger, frischer, fruchtiger und/oder süßer Note) und/oder sonstige übliche Zusatzstoffe können vorhanden sein. Apply the mixture to the hair or textile fibers. A surfactant-containing mixture, in particular a solution which comprises: (a) water, (b) 2-methoxymethylphenol (for example, for example), is particularly suitable for the uses according to the invention or the corresponding processes which relate to the treatment of hair or textile fibers. in the form of a fragrance combination according to the invention) and (c) one or more surfactants, the concentration of 2-methoxymethylphenol in the solution being in the range from 10 ~ 7-10 ~ 1 % by weight. Other fragrances (as part of a fragrance composition according to the invention, in particular one with a vanilla, carnation, leathery, fresh, fruity and / or sweet note) and / or other conventional additives may be present.
Bevorzugte erfindungsgemäße Produkte sind (a) Parfümölmischungen (als Beispiel für erfindungsgemäße Riechstoffkompositionen) für tensidhaltige Formulierungen, wie z.B. Reinigungsmittel, Waschmittel, Weichspüler sowie Körperpflegemittel sowie (b) die entsprechenden tensidhaltigen Formulierungen selbst. Die bevorzugten tensidhaltigen Formulierungen, die im Rahmen der vorliegenden Erfindung eingesetzt werden können, umfassen neben den erfindungsgemäßen Riechstoffkompositionen allgemein Substanzen aus der Klasse der anionischen Tenside, wie zum Beispiel Carboxylate, Sulfate, Sulfonate und Phosphate, der kationischen Tenside, wie zum Beispiel quartäre Ammoniumsalze, der amphote- ren Tenside, wie zum Beispiel Betaine, und der nichtionischen Tenside, wie zum Beispiel Ethoxylate und Propoxylate. Preferred products according to the invention are (a) perfume oil mixtures (as an example for fragrance compositions according to the invention) for formulations containing surfactants, such as e.g. Cleaning agents, detergents, fabric softeners and personal care products and (b) the corresponding surfactant-containing formulations themselves. The preferred surfactant-containing formulations which can be used in the context of the present invention generally comprise, in addition to the fragrance compositions according to the invention, substances from the class of anionic surfactants, such as carboxylates , Sulfates, sulfonates and phosphates, the cationic surfactants such as quaternary ammonium salts, the amphoteric surfactants such as betaines, and the nonionic surfactants such as ethoxylates and propoxylates.
Unter den anionischen Tensiden sind die Sulfate und Sulfonate bevorzugt. Bei den Sulfaten sind solche mit 12 bis 18 Kohlenstoffatomen und einem Ethoxylie- rungsgrad von 1 bis maximal 5 bevorzugt. Insbesondere bevorzugt ist Natrium- laurylethersulfat, vorzugsweise mit einem mittleren Ethoxylierungsgrad von 2 bis 4. The sulfates and sulfonates are preferred among the anionic surfactants. In the case of the sulfates, those having 12 to 18 carbon atoms and a degree of ethoxylation of 1 to a maximum of 5 are preferred. Sodium lauryl ether sulfate is particularly preferred, preferably with an average degree of ethoxylation of 2 to 4.
Unter den Sulfonaten sind insbesondere die linearen Natriumalkylbenzolsulfona- te mit durchschnittlich ca. 12 Kohlenstoffatomen in der Alkylkette, wobei diese aus homologen Resten mit 10 bis 14 Kohlenstoffatomen bestehen („Dodecylben- zolsulfonat"), bevorzugt. Aus der Gruppe der nichtionischen Tenside sind die ethoxylierten Fettalkohole, die durch Ethoxylierung von Alkoholen mit 12 bis 18 Kohlenstoffatomen erhalten werden (Fettalkoholethoxylate mit 12 bis 18 C-Atomen), bevorzugt. Der Ethoxy- lierungsgrad kann dabei in weiten Grenzen variieren, besonders bevorzugt sind jedoch Produkte mit einem durchschnittlichen Ethoxylierungsgrad von 5 bis 10, insbesondere von 7 Mol addiertem Ethylenoxid pro Mol Fettalkohol. Among the sulfonates, the linear sodium alkylbenzenesulfonates with an average of about 12 carbon atoms in the alkyl chain are particularly preferred, these consisting of homologous residues with 10 to 14 carbon atoms (“dodecylbenzenesulfonate”). From the group of nonionic surfactants, the ethoxylated fatty alcohols which are obtained by ethoxylating alcohols with 12 to 18 carbon atoms (fatty alcohol ethoxylates with 12 to 18 C atoms) are preferred. The degree of ethoxylation can vary within wide limits, but products with an average degree of ethoxylation of 5 to 10, in particular 7 moles of added ethylene oxide per mole of fatty alcohol are particularly preferred.
Unter den Betainen sind insbesondere solche vom Säureamidtyp mit der aufgeführten Struktur bevorzugt. Among the betaines, those of the acid amide type with the structure listed are particularly preferred.
Figure imgf000018_0001
Ein bevorzugter Rest RC=O ist dabei der Schnitt aus den Fettsäuren des Kokosöls, in dem die Laurylsäure mit 45-50% der Hauptbestandteil ist.
Figure imgf000018_0001
A preferred radical RC = O is the cut from the fatty acids of coconut oil, in which the main constituent is lauric acid with 45-50%.
In Kombination mit ausgewählten Tensiden sind die günstigen Eigenschaften des 2-Methoxymethylphenols überraschend stark ausgeprägt. Eine entsprechende erfindungsgemäße Tensidformulierung (als Beispiel eines erfindungsgemäßen Artikels) umfasst 2-Methoxymethylphenol und ein oder mehrere Tenside, die ausgewählt sind aus der Gruppe bestehend aus: In combination with selected surfactants, the favorable properties of 2-methoxymethylphenol are surprisingly strong. A corresponding surfactant formulation according to the invention (as an example of an article according to the invention) comprises 2-methoxymethylphenol and one or more surfactants which are selected from the group consisting of:
Lineare Alkylbenzolsulfonate (insbesondere die oben genannten, wie z.B. die linearen Natriumalkylbenzolsulfonate), Linear alkylbenzenesulfonates (especially those mentioned above, such as the linear sodium alkylbenzenesulfonates),
Fettalkoholethoxylate mit 12-18 C-Atomen (insbesondere die oben genann- ten, also z.B. die mit dem oben als bevorzugt gekennzeichneten Ethoxylierungsgrad), Fatty alcohol ethoxylates with 12-18 C atoms (in particular those mentioned above, i.e. for example those with the degree of ethoxylation designated above as preferred),
Laurylethersulfate (insbesondere die oben genannten, also z.B. das oben genannte Natriumlaurylethersulfat) und Betaine (insbesondere die oben genannten, also z.B. Betaine vom Säurea- midtyp mit der oben aufgeführten Struktur). Lauryl ether sulfates (in particular those mentioned above, for example the sodium lauryl ether sulfate mentioned above) and Betaines (in particular those mentioned above, for example betaines of the acid amide type with the structure listed above).
Lineare Alkylbenzolsulfonate und Fettalkoholethoxylate mit 12-18 C-Atomen werden dabei vorzugsweise nebeneinander eingesetzt, insbesondere in VoII- waschmittelpulvern. Linear alkylbenzenesulfonates and fatty alcohol ethoxylates with 12-18 C atoms are preferably used next to one another, in particular in detergent powders.
Ebenso werden Laurylethersulfate (insbesondere das oben genannte Natrium- laurylethersulfat) und Betaine (insbesondere Betaine vom Säureamidtyp mit der oben aufgeführten Struktur) vorzugsweise nebeneinander eingesetzt, insbesondere in Feinwaschmitteln, Shampoos und Duschgelen. Die Konzentration der oberflächenaktiven Stoffe in den erfindungsgemäßen Tensidformulierungen ist in der Regel unkritisch. Bevorzugte Konzentrationen sind abhängig vom Typ des Tensids und der jeweiligen Anwendung. Sie können zum Beispiel in speziellen Bleichprodukten kleiner 1 Gew.-%, in Seifen oder Waschpulver aber größer 99 Gew.-% sein. Für bestimmte Anwendungsgebiete sind in erfindungsgemäßen Tensidformulierungen bestimmte Kombinationen und Konzentrationen bevorzugt. So sind erfindungsgemäße Mischungen (Waschmittelformulierungen) bevorzugt, in denen der Anteil an linearen Alkylbenzolsulfonaten im Bereich von 7 - 10 Gew.-% und/oder der Anteil an Fettalkoholethoxylaten mit 12-18 C-Atomen im Bereich von 3 - 6 Gew.-% liegt, jeweils bezogen auf die Gesamtmasse der Mischung. Zudem sind erfindungsgemäße Mischungen (Formulierungen für Feinwaschmittel, Shampoos und Duschgele) bevorzugt, in denen der Anteil an Natriumlaurylethersulfat im Bereich von 7 - 13 Gew.-% und/oder der Anteil an Betain (insbesondere Betain vom Säureamidtyp mit der oben aufgeführten Struktur) im Bereich von 1 - 3 Gew.-% liegt, jeweils bezogen auf die Gesamtmasse der Mischung. Likewise, lauryl ether sulfates (in particular the above-mentioned sodium lauryl ether sulfate) and betaines (in particular betaines of the acid amide type with the structure listed above) are preferably used next to one another, in particular in mild detergents, shampoos and shower gels. The concentration of the surface-active substances in the surfactant formulations according to the invention is generally not critical. Preferred concentrations depend on the type of surfactant and the particular application. For example, they can be less than 1% by weight in special bleaching products, but more than 99% by weight in soaps or washing powder. For certain fields of application, certain combinations and concentrations are preferred in surfactant formulations according to the invention. Mixtures according to the invention (detergent formulations) are preferred in which the proportion of linear alkylbenzenesulfonates in the range from 7 to 10% by weight and / or the proportion of fatty alcohol ethoxylates with 12-18 C atoms in the range from 3 to 6% by weight is based on the total mass of the mixture. Mixtures according to the invention (formulations for mild detergents, shampoos and shower gels) are also preferred in which the proportion of sodium lauryl ether sulfate is in the range from 7 to 13% by weight and / or the proportion of betaine (in particular betaine of the acid amide type with the structure listed above) Range of 1 - 3 wt .-%, based in each case on the total mass of the mixture.
Bei Anwendung erfindungsgemäßer Tensidformulierungen ist die Substantivität des 2-Methoxymethylphenols auf Haaren und textilen Fasern derart ausgeprägt, dass der Eindruck entsteht, dass die vorhandenen Tenside das 2- Methoxymethylphenol zwar zunächst in die wässrige Phase hineinbringen, diese Verbindung jedoch in Gegenwart von Haaren oder textilen Fasern aus der wäss- rigen Phase heraus- und auf die Haare bzw. die textile Faser gedrängt wird. Eine wissenschaftliche Erklärung für diese Beobachtung gibt es jedoch derzeit nicht. When using surfactant formulations according to the invention, the substantivity of the 2-methoxymethylphenol on hair and textile fibers is so pronounced that the impression arises that the surfactants present bring the 2-methoxymethylphenol into the aqueous phase first, but this compound in the presence of hair or textile fibers from the water phase and pushed onto the hair or textile fiber. However, there is currently no scientific explanation for this observation.
Neben seinen Eigenschaften als "Booster" und seinem hohen Aufziehvermögen zeichnet sich 2-Methoxymethylphenol durch seine fixierenden Eigenschaften aus. Ein solcher Fixateur erhöht die Haftfestigkeit von anderen Riechstoffen, sei es durch deren Dampfdruckerniedrigung oder geruchliche Verstärkung (z.B. Absenkung des Schwellenwertes). Die Erfindung betrifft daher auch - wie bereits erwähnt - die Verwendung von 2-Methoxymethylphenol oder einer 2- Methoxymethylphenol umfassenden Riechstoffmischung (wie oben charakteri- siert) als Fixateur. In addition to its properties as a "booster" and its high absorbency, 2-methoxymethylphenol is characterized by its fixing properties. Such a fixator increases the adhesive strength of other fragrances, whether by lowering their vapor pressure or enhancing their odor (e.g. lowering the threshold value). The invention therefore also relates, as already mentioned, to the use of 2-methoxymethylphenol or a fragrance mixture comprising 2-methoxymethylphenol (as characterized above) as a fixator.
Die Herstellung von 2-Methoxymethylphenol erfolgt vorzugsweise nach einer der oben beschriebenen Veretherungsmethoden ausgehend von Salicylalkohol. 2-Methoxymethylphenol is preferably prepared using one of the etherification methods described above, starting from salicyl alcohol.
2-Methoxymethylphenol wurde in eigenen Untersuchungen beispielsweise ausgehend von Salicylaldehyd durch Reduktion mit Natriumborhydrid und anschlie- ßende Veretherung des entstandenen Salicylalkohols mit Methanol in Gegenwart von Schwefelsäure hergestellt (vergleiche Beispiel 1 , unten):
Figure imgf000020_0001
In our own investigations, 2-methoxymethylphenol was produced, for example, from salicylaldehyde by reduction with sodium borohydride and subsequent etherification of the salicyl alcohol formed with methanol in the presence of sulfuric acid (see Example 1, below):
Figure imgf000020_0001
2-Methoxymethylphenol eignet sich wegen seiner olfaktorischen Eigenschaften vorzüglich für den Einsatz in Riech- und Aromastoffkompositionen. Die Verbin- düng kann mit einer Vielzahl weiterer Riech- oder Aromastoffe kombiniert in zahlreichen Produkten verwendet werden. Besonders vorteilhaft lässt sich die Verbindung mit anderen Riech- oder Aromastoffen in verschiedenen, unterschiedlichen Mengenverhältnissen zu neuartigen Riech- oder Aromastoffkompositionen kombinieren. Es ist vorteilhaft, 2-Methoxymethylphenol zumindest mit einem weiteren Riechoder Aromastoff zu kombinieren und so eine neue Riech- oder Aromastoffkomposition zu bilden; vorzugsweise umfassen die weiteren Riech- oder Aroma- stoff dabei eine oder mehrere der in Tabelle 2 aufgeführten Verbindungen. Auf diese Weise lassen sich besonders interessante und natürliche neue und originelle Duftnoten kreieren. Riechstoffe, die zur Kombination vorteilhafterweise geeignet sind, finden sich z.B. in S. Arctander, Perfume and Flavor Materials, Vol. I und II, Montclair, N. J. 1969, Eigenverlag, oder K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001. Im einzelnen seien genannt: Because of its olfactory properties, 2-methoxymethylphenol is particularly suitable for use in fragrance and flavoring compositions. The compound can be used in numerous products in combination with a large number of other fragrance or aroma substances. The compound can be combined particularly advantageously with other odoriferous or aromatic substances in different, different proportions to form novel odoriferous or aromatic substance compositions. It is advantageous to combine 2-methoxymethylphenol with at least one other fragrance or flavoring agent and thus to form a new fragrance or flavoring agent composition; preferably the further smelling or aromatic substance one or more of the compounds listed in Table 2. In this way, particularly interesting and natural new and original fragrance notes can be created. Fragrances that are advantageously suitable for combination can be found, for example, in 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. The following may be mentioned in detail:
Extrakte aus natürlichen Rohstoffen wie Etherische Öle, Concretes, Absolues, Resine, Resinoide, Balsame, Tinkturen wie z. B. Ambratinktur; Amyrisöl; Angelicasamenöl; Angelicawurzelöl; Anisöl; Baldrianöl; Basilikumöl; Baummoos -Absolue; Bayöl; Beifußöl; Benzoeresin; Bergamotteöl; Bienenwachs-Absolue; Birkenteeröl; Bittermandelöl; Bohnenkrautöl; Buccoblätte- röl; Cabreuvaöl; Cadeöl; Calmusöl; Campheröl; Canangaöl; Cardamomenöl; Cascarillaöl; Cassiaöl; Cassie-Absolue; Castoreum-absolue; Cedernblätteröl; Cedernholzöl; Cistusöl; Citronellöl; Citronenöl; Copaivabalsam; Copaivabalsa- möl; Corianderöl; Costuswurzelöl; Cuminöl; Cypressenöl; Davanaöl; Dillkrautöl; Dillsamenöl; Eau de brouts-Absolue; Eichenmoos-Absolue; Elemiöl; Estragonöl; Eucalyptus-citriodora-ÖI; Eucalyptusöl; Fenchelöl ; Fichtennadelöl; Galbanumöl; Galbanumresin; Geraniumöl; Grapefruitöl; Guajakholzöl; Gurjunbalsam; Gurjun- balsamöl; Helichrysum-Absolue; Helichrysumöl; Ingweröl; Iriswurzel-Absolue; Iriswurzelöl; Jasmin-Absolue; Kalmusöl; Kamillenöl blau; Kamillenöl römisch; Karottensamenöl; Kaskarillaöl; Kiefernadelöl; Krauseminzöl; Kümmelöl; Labda- numöl; Labdanum-Absolue; Labdanumresin; Lavandin-Absolue; Lavandinöl ; Lavendel-Absolue; Lavendelöl; Lemongrasöl; Liebstocköl; Limetteöl destilliert; Limetteöl gepreßt; Linaloeöl; Litsea-cubeba-ÖI; Lorbeerblätteröl; Macisöl; Majo- ranöl; Mandarinenöl; Massoirindenöl; Mimosa-Absolue; Moschuskörneröl; Moschustinktur; Muskateller-Salbei-Öl; Muskatnußöl; Myrrhen-Absolue; Myrrhenöl; Myrtenöl; Nelkenblätteröl; Nelkenblütenöl; Neroliöl; Olibanum-Absolue; Olibanu- möl; Opopanaxöl; Orangenblüten-Absolue; Orangenöl; Origanumöl; Palmarosaöl; Patchouliöl; Perillaöl; Perubalsamöl; Petersilienblätteröl; Petersiliensamenöl; Petitgrainöl; Pfefferminzöl; Pfefferöl; Pimentöl; Pineöl; Poleyöl; Rosen-Absolue; Rosenholzöl; Rosenöl; Rosmarinöl; Salbeiöl dalmatinisch; Salbeiöl spanisch; Sandelholzöl; Selleriesamenöl; Spiklavendelöl; Sternanisöl; Styraxöl; Tagetesöl; Tannennadelöl; Tea-tree-ÖI; Terpentinöl; Thymianöl; Tolubalsam; Tonka- Absolue; Tuberosen-Absolue; Vanilleextrakt; Veilchenblätter-Absolue; Verbenaöl; Vetiveröl; Wacholderbeeröl; Weinhefenöl; Wermutöl; Wintergrünöl; Ylangöl; Ysopöl; Zibet-Absolue; Zimtblätteröl; Zimtrindenöl sowie Fraktionen davon, bzw. daraus isolierten Inhaltsstoffen; 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; Copaivabalsam oil; Coriander oil; Costus root oil; Cumin oil; Cypress oil; Davana oil; Dill herb oil; Dill seed oil; Eau de brouts absolute; Oakmoss absolute; Elemi oil; Tarragon oil; Eucalyptus citriodora oil; Eucalyptus oil; Fennel oil; Spruce needle oil; Galbanum oil; Galbanumresin; Geranium oil; Grapefruit oil; Guaiac wood oil; Gurjun balm; Gurjun balsam oil; Helichrysum absolute; Helichrysum oil; Ginger oil; Iris root absolute; Iris root oil; Jasmine absolute; Calamus oil; Chamomile oil blue; Roman chamomile oil; Carrot seed oil; Cascilla oil; Pine oil; Spearmint oil; Caraway oil; Labdana oil; Labdanum absolute; Labdanumresin; Lavandin absolute; Lavandin oil; Lavender absolute; Lavender oil; Lemongrass oil; Loving stick oil; Distilled lime oil; Lime oil pressed; Linaloe oil; Litsea cubeba oil; Bay leaf oil; Mace oil; Mayonnaise oil; Mandarin oil; Massoir oil; Mimosa absolute; Musk grain oil; Musk tincture; Muscat Sage Oil; Nutmeg oil; Myrrh absolute; Myrrh oil; Myrtle oil; Clove leaf oil; Clove flower oil; Neroli oil; Olibanum absolute; Olibanum oil; Opopanax oil; Orange blossom absolute; Orange oil; Original oil; Palmarosa oil; Patchouli oil; Perilla oil; Peru balsam oil; Parsley leaf oil; Parsley seed oil; Petitgrain oil; Peppermint oil; Pepper oil; Allspice oil; Pine oil; Poley oil; Rose absolute; Rosewood oil; Rose oil; Rosemary oil; Dalmatian sage oil; Sage oil spanish; Sandalwood oil; Celery seed oil; Spiklavendel oil; Star anise oil; Styrax oil; Tagetes oil; Pine needle oil; Tea tree oil; Turpentine oil; Thyme oil; Tolu balm; Tonka absolute; Tuberose absolute; Vanilla extract; Violet leaf absolute; Verbena oil; Vetiver oil; Juniper berry oil; Wine yeast oil; Wormwood oil; Wintergreen oil; Ylang oil; Hyssop oil; Cibet absolute; Cinnamon leaf oil; Cinnamon bark oil and fractions thereof, or ingredients isolated from them;
Einzel-Riechstoffe aus der Gruppe der Kohlenwasserstoffe, wie z.B. 3-Caren; alpha-Pinen; beta-Pinen; alpha-Terpinen; gamma-Terpinen; p-Cymol; Bisabolen; Camphen; Caryophyllen; Cedren; Farnesen; Limonen; Longifolen; Myrcen; Oci- men; Valencen; (E1Z)-1 , 3, 5-Undecatrien; Styrol; Diphenylmethan; der aliphatischen Alkohole wie z.B. Hexanol; Octanol; 3-Octanol; 2,6- Dimethylheptanol; 2-Methyl-2-heptanol; 2-Methyl-2-octanol; (E)-2-Hexenol; (E)- und (Z)-3-Hexenol; 1 -Octen-3-ol; Gemisch von 3,4,5,6,6-Pentamethyl-3/4- hepten-2-ol und 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; der aliphatischen Aldehyde und deren Acetale wie z.B. Hexanal; Heptanal; Octa- nal; Nonanal; Decanal; Undecanal; Dodecanal; Tridecanal; 2-Methyloctanal; 2- Methylnonanal; (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-hexen; Citronellyloxyacetaldehyd; 1 -(1 -Methoxy-propoxy)-(E/Z)-3- hexen; der aliphatischen Ketone und deren Oxime wie z.B. 2-Heptanon; 2-Octanon; 3- Octanon; 2-Nonanon; 5-Methyl-3-heptanon ; 5-Methyl-3-heptanonoxim; 2,4,4,7- Tetramethyl-6-octen-3-on; 6-Methyl-5-hepten-2-on; der aliphatischen schwefelhaltigen Verbindungen wie z.B. 3-Methylthio-hexanol; 3-Methylthiohexylacetat; 3-Mercaptohexanol; 3-Mercaptohexylacetat; 3- Mercaptohexylbutyrat; 3-Acetylthiohexylacetat; 1-Menthen-8-thiol; der aliphatischen Nitrile wie z.B. 2-Nonensäurenitril; 2-Undecensäurenitril; 2- Tridecensäurenitril; 3,12-Tridecadiensäurenitril; 3,7-Dimethyl-2,6-octadien- säurenitril; 3,7-Dimethyl-6-octensäurenitril; der Ester von aliphatischen Carbonsäuren wie z.B. (E)- und (Z)-3-Hexenylformiat;Individual fragrances from the group of hydrocarbons, such as 3-carene; alpha-pinene; beta-pinene; alpha terpinene; gamma terpinene; p-cymene; Bisabolene; Camphene; Caryophyllene; Cedren; Farnese; Lime; Longifolene; Myrcene; Ocimen; Valencene; (E 1 Z) -1, 3, 5-undecatriene; Styrene; Diphenylmethane; aliphatic alcohols such as 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-methoxyoctan-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; Heptanal diethylacetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; Citronellyloxyacetaldehyde; 1 - (1-methoxy-propoxy) - (E / Z) -3-hexene; aliphatic ketones and their oximes such as 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 as 3-methylthio-hexanol; 3-methylthiohexyl acetate; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthen-8-thiol; aliphatic nitriles such as 2-nonenenitrile; 2-undecenonitrile; 2-tridecenonitrile; 3,12-tridecadienonitrile; 3,7-dimethyl-2,6-octadienonitrile; 3,7-dimethyl-6-octenonitrile; the ester of aliphatic carboxylic acids such as (E) - and (Z) -3-hexenyl formate;
Ethylacetoacetat; Isoamylacetat; Hexylacetat; 3,5,5-Trimethylhexylacetat; 3-Ethyl acetoacetate; Isoamyl acetate; Hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-
Methyl-2-butenylacetat; (E)-2-Hexenylacetat; (E)- und (Z)-3-Hexenylacetat; Octy- lacetat; 3-Octylacetat; 1-Octen-3-ylacetat; Ethylbutyrat; Butylbutyrat, ; Isoamylbu- tyrat; Hexylbutyrat; (E)- und (Z)-3-Hexenyl-isobutyrat; Hexylcrotonat; Ethylisova- lerianat; Ethyl-2-methylpentanoat; Ethylhexanoat; Allylhexanoat; Ethylheptanoat;Methyl 2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenyl acetate; Octyl acetate; 3-octyl acetate; 1-octen-3-ylacetate; Ethyl butyrate; Butyl butyrate,; Isoamyl butyrate; Hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate; Hexyl crotonate; Ethyl isomerate; Ethyl 2-methylpentanoate; Ethyl hexanoate; Allyl hexanoate; Ethyl heptanoate;
Allylheptanoat; Ethyloctanoat; Ethyl-(E,Z)-2,4-decadienoat; Methyl-2-octinat;Allyl heptanoate; Ethyl octanoate; Ethyl (E, Z) -2,4-decadienoate; Methyl 2-octinate;
Methyl-2-noninat; Allyl-2-isoamyloxyacetat; Methyl-3,7-dimethyl-2,6- octadienoat;4-Methyl-2-pentyl-crotonat; der acyclischen Terpenalkohole wie z. B. Citronellol; Geraniol; Nerol; Linalool; Lavadulol; Nerolidol; Farnesol; Tetrahydrolinalool; Tetrahydrogeraniol; 2,6- Dimethyl-7-octen-2-ol; 2,6-Dimethyloctan-2-ol; 2-Methyl-6-methylen-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-1 ,5,7-octatrien-3-ol 2,6-Dimethyl-2,5,7-octatrien-1-ol; sowie deren Formiate, Acetate, Propionate, Isobutyrate, Butyrate, Isovalerianate, Pentanoate, Hexanoate, Crotonate, Tiglinate und 3-Methyl-2-butenoate; der acyclischen Terpenaldehyde und -ketone wie z. B. Geranial; Neral; Citronel- IaI; 7-Hydroxy-3,7-dimethyloctanal; 7-Methoxy-3,7-dimethyloctanal; 2,6,10- Trimethyl-9-undecenal; Geranylaceton; sowie die Dimethyl- und Diethylacetale von Geranial, Neral, 7-Hydroxy-3,7-dimethyloctanal; der cyclischen Terpenalkohole wie z. B. Menthol; Isopulegol; alpha-Terpineol; Terpinenol-4; Menthan-8-ol; Menthan-1-ol; Menthan-7-ol; Borneol; Isoborneol; Linalooloxid; Nopol; Cedrol; Ambrinol; Vetiverol; Guajol; sowie deren Formiate, Acetate, Propionate, Isobutyrate, Butyrate, Isovalerianate, Pentanoate, Hexanoa- te, Crotonate, Tiglinate und 3-Methyl-2-butenoate; der cyclischen Terpenaldehyde und -ketone wie z. B. Menthon; Isomenthon ; 8- Mercaptomenthan-3-on ; Carvon; Campher; Fenchon; alpha-lonon; beta-lonon; alpha-n-Methylionon; beta-n-Methylionon; alpha-lsomethylionon; beta- Isomethylionon; alpha-lron; alpha-Damascon; beta-Damascon; beta- Damascenon; delta-Damascon; gamma-Damascon; 1 -(2,4,4-Trimethyl-2- cyclohexen-1 -yl)-2-buten-1 -on; 1 ,3,4,6,7,8a-Hexahydro-1 , 1 ,5,5-tetramethyl-2H- 2,4a-methanonaphthalen-8(5H)-on;2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1- yl)-2-butenal; Nootkaton ; Dihydronootkaton ; 4,6,8-Megastigmatrien-3-on; alpha- Sinensal ; beta-Sinensal ; acetyliertes Cedernholzöl (Methylcedrylketon); der cyclischen Alkohole wie z.B. 4-tert.-Butylcyclohexanol ; 3,3,5- Trimethylcyclohexanol; 3-lsocamphylcyclohexanol; 2,6,9-Trimethyl-Z2,Z5,E9- cyclododecatrien-1-ol; 2-lsobutyl-4-methyltetrahydro-2H-pyran-4-ol; der cycloaliphatischen Alkohole wie z.B. alpha, 3,3-Methyl 2-noninate; Allyl-2-isoamyloxyacetate; Methyl 3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl crotonate; the acyclic terpene alcohols such as B. Citronellol; Geraniol; Nerol; Linalool; Lavadulol; Nerolidol; Farnesol; Tetrahydrolinalool; Tetrahydrogeraniol; 2,6-dimethyl-7-octen-2-ol; 2,6-dimethyloctan-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-1,5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octatrien-1-ol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoate; the acyclic terpene aldehydes and ketones such as B. Geranial; Neral; Citronel IaI; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; Geranylacetone; as well as the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal; the cyclic terpene alcohols such as B. menthol; Isopulegol; alpha-terpineol; Terpinenol-4; Menthan-8-ol; Menthan-1-ol; Menthan-7-ol; Borneol; Isoborneol; Linalool oxide; Nopol; Cedrol; Ambrinol; Vetiverol; Guajol; as well as their formats, Acetates, propionates, isobutyrates, butyrates, isovalerianates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoate; the cyclic terpene aldehydes and ketones such. B. Menthon; Isomenthon; 8-mercaptomenthan-3-one; Carvon; Camphor; Fenchone; alpha-lonon; beta-lonon; alpha-n-methyl ionone; beta-n-methyl ionone; alpha-isomethylionone; beta-isomethyl ionone; alpha-lron; alpha damascon; beta-damascon; beta damascenon; delta-damascon; gamma-damascon; 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; 2-methyl-4- (2,6, 6-trimethyl-1-cyclohexen-1-yl) -2-butenal; Nootcat; Dihydronootcatone; 4,6,8-megastigatrien-3-one; 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-1-ol; 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol; cycloaliphatic alcohols such as alpha, 3,3-
Trimethylcyclohexylmethanol;1-(4-lsopropylcyclohexyl)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; 2-Ethyl-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-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; 2-ethyl-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; der cyclischen und cycloaliphatischen Ether wie z.B. Cineol; Cedrylmethylether; Cyclododecylmethylether;1 ,1-Dimethoxycyclododecan; (Ethoxymetho- xy)cyclododecan; alpha-Cedrenepoxid; 3a, 6, 6,9a-Trimethylcyclohexyl) hexan-3-ol; cyclic and cycloaliphatic ethers such as e.g. Cineol; Cedryl methyl ether; Cyclododecyl methyl ether; 1, 1-dimethoxycyclododecane; (Ethoxymethoxy) cyclododecane; alpha-cedrenepoxide; 3a, 6, 6,9a-
Tetramethyldodecahydronaphtho[2,1 -b]furan; 3a-Ethyl-6,6,9a- trimethyldodecahydronaphtho[2,1-b]furan; 1 ,5,9-Trimethyl-13- oxabicyclo[10.1.0]trideca-4,8-dien; Rosenoxid; 2-(2,4-Dimethyl-3-cyclohexen-1- yl)-5-methyl-5-(1 -methylpropyl)-1 ,3-dioxan; der cyclischen und makrocyclischen Ketone wie z.B. 4-tert.-Butylcyclohexanon; 2,2,5-Trimethyl-5-pentylcyclopentanon; 2-Heptylcyclopentanon; 2-Tetramethyldodecahydronaphtho [2,1 -b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2,1-b] furan; 1,5,9-trimethyl-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-dioxane; cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-
Pentylcyclopentanon; 2-Hydroxy-3-methyl-2-cyclopenten-1-on; 3-Methyl-cis-2- penten-1-yl-2-cyclopenten-1-on; 3-Methyl-2-pentyl-2-cyclopenten-1-on; 3-Methyl- 4-cyclopentadecenon; S-Methyl-δ-cyclopentadecenon; 3-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; S-methyl-δ-cyclopentadecenone; 3-
Methylcyclopentadecanon; 4-(1 -Ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanon; 4- tert.-Pentylcyclohexanon; 5-Cyclohexadecen-1-on; 6,7-Dihydro-1 ,1 ,2,3,3- pentamethyl-4(5H)-indanon; 8-Cyclohexadecen-1-on; θ-Cycloheptadecen-i-on; Cyclopentadecanon; Cyclohexadecanon; der cycloaliphatischen Aldehyde wie z.B. 2,4-Dimethyl-3-cyclohexencarbaldehyd; 2-Methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-Hydroxy-4- methylpentyl)-3-cyclohexencarbaldehyd; 4-(4-Methyl-3-penten-1-yl)-3- cyclohexencarbaldehyd; der cycloaliphatischen Ketone wie z. B. 1-(3,3-Dimethylcyclohexyl)-4-penten-1- on; 2,2-Dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanon; 1 -(5,5-Dimethyl- 1-cyclohexen-1-yl)-4-penten-1-on; 2,3,8,8-Tetramethyl-1 ,2,3,4,5,6,7,8-octahydro- 2-naphtalenylmethylketon; Methyl^.θ.iO-trimethyl^.δ.θ-cyclododecatrienylketon; tert.-Butyl-(2,4-dimethyl-3-cyclohexen-1-yl)keton; der Ester cyclischer Alkohole wie z.B. 2-tert-Butylcyclohexylacetat; 4-tert- Butylcyclohexylacetat; 2-tert-Pentylcyclohexylacetat; 4-tert-Methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-dihydro-1,1,3,3-pentamethyl-4 (5H) -indanone; 8-cyclohexadecen-1-one; θ-cycloheptadecen-i-one; Cyclopentadecanone; Cyclohexadecanone; cycloaliphatic aldehydes such as e.g. 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-1-yl) -3-cyclohexenecarbaldehyde; the 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 ^ .θ.iO-trimethyl ^ .δ.θ-cyclododecatrienyl ketone; tert-butyl- (2,4-dimethyl-3-cyclohexen-1-yl) ketone; the esters of cyclic alcohols such as e.g. 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert
Pentylcyclohexylacetat; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2- naphthylacetat;2-Cyclopentylcyclopentylcrotonat; 3-Pentyltetrahydro-2H-pyran-4- ylacetat; Decahydro-2,5,5,8a-tetramethyl-2-naphthylacetat; 4,7-Methano-Pentylcyclohexyl acetate; 3,3,5-trimethylcyclohexyl acetate; Decahydro-2-naphthyl acetate; 2-cyclopentylcyclopentyl crotonate; 3-pentyltetrahydro-2H-pyran-4-ylacetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthylacetate; 4,7-methano
3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylacetat; 4,7-Methano-3a,4,5,6,7,7a- hexahydro-5, bzw. 6-indenylpropionat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylisobutyrat; 4,7-Methanooctahydro-5, bzw. 6-indenylacetat; der Ester cycloaliphatischer Alkohole wie z.B.I -Cyclohexylethylcrotonat; der Ester cycloaliphatischer Carbonsäuren wie z. B. Allyl-3-cyclohexylpropionat;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; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, or 6-indenyl isobutyrate; 4,7-methanooctahydro-5 or 6-indenyl acetate; the ester of cycloaliphatic alcohols such as I-cyclohexylethyl crotonate; the ester of cycloaliphatic carboxylic acids such as. B. allyl-3-cyclohexylpropionate;
Allylcyclohexyloxyacetat; eis - und trans-Methyldihydrojasmonat; eis- und trans- Methyljasmonat; Methyl-2-hexyl-3-oxocyclopentancarboxylat; Ethyl-2-ethyl-6,6- dimethyl-2-cyclohexencarboxylat; Ethyl-2,3,6,6-tetramethyl-2- cyclohexencarboxylat; Ethyl-2-methyl-1 ,3-dioxolan-2-acetat; der araliphatischen Alkohole wie z.B. Benzylalkohol; 1-Phenylethylalkohol; 2- Phenylethylalkohol; 3-Phenylpropanol; 2-Phenylpropanol; 2-Phenoxyethanol; 2,2- Dimethyl-3-phenylpropanol; 2,2-Dimethyl-3-(3-methylphenyl)propanol; 1 ,1 - Dimethyl-2-phenylethylalkohol; 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-Methoxybenzylalkohol; 1 -(4-lsopropylphenyl)ethanol; der Ester von araliphatischen Alkoholen und aliphatischen Carbonsäuren wie z.B. Benzylacetat; Benzylpropionat; Benzylisobutyrat; Benzylisovalerianat; 2- Phenylethylacetat; 2-Phenylethylpropionat; 2-Phenylethylisobutyrat; 2- Phenylethylisovalerianat; 1 -Phenylethylacetat; alpha-Trichlormethylbenzylacetat; alpha, alpha-Dimethylphenylethylacetat; alpha, alpha-Dimethylphenylethylbutyrat; Cinnamylacetat; 2-Phenoxyethylisobutyrat; 4-Methoxybenzylacetat; der araliphatischen Ether wie z.B. 2-Phenylethylmethylether; 2- Phenylethylisoamylether; 2-Phenylethyl-1 -ethoxyethylether; Phenylacetaldehyd- dimethylacetal; Phenylacetaldehyddiethylacetal; Hydratropaaldehyddimethylace- tal; Phenylacetaldehydglycerinacetal; 2,4,6-Trimethyl-4-phenyl-1 ,3-dioxan; 4,4a,5,9b-Tetrahydroindeno[1 ,2-d]-m-dioxin; 4,4a,5,9b-Tetrahydro-2,4- dimethylindeno[1 ,2-d]-m-dioxin; der aromatischen und araliphatischen Aldehyde wie z. B. Benzaldehyd; Phenyla- cetaldehyd; 3-Phenylpropanal; Hydratropaaldehyd; 4-Methylbenzaldehyd; 4- Methylphenylacetaldehyd; 3-(4-Ethylphenyl)-2,2-dimethylpropanal; 2-Methyl-3-(4- isopropylphenyl)propanal; 2-Methyl-3-(4-tert.-butylphenyl)propanal; 2-Methyl-3- (4-isobutylphenyl)propanal; 3-(4-tert.-Butylphenyl)propanal; Zimtaldehyd; alpha- Butylzimtaldehyd; alpha-Amylzimtaldehyd; alpha-Hexylzimtaldehyd; 3-Methyl-5- phenylpentanal; 4-Methoxybenzaldehyd; 4-Hydroxy-3-methoxybenzaldehyd; 4- Hydroxy-3-ethoxybenzaldehyd; 3,4-Methylendioxybenzaldehyd; 3,4-Allylcyclohexyloxyacetate; 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-phenylethyl alcohol; 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 alcohol; 1 - (4-isopropylphenyl) ethanol; the ester of araliphatic alcohols and aliphatic carboxylic acids such as benzyl acetate; Benzyl propionate; Benzyl isobutyrate; Benzyl isovalerate; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-phenylethyl isobutyrate; 2-phenylethyl isovalerate; 1-phenylethyl acetate; alpha-trichloromethylbenzyl acetate; alpha, alpha-dimethylphenylethyl acetate; alpha, alpha-dimethylphenylethyl butyrate; Cinnamate acetate; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate; the araliphatic ether such as 2-phenylethyl methyl ether; 2-phenylethyl isoamyl ether; 2-phenylethyl-1-ethoxyethyl ether; Phenylacetaldehyde dimethyl acetal; Phenylacetaldehyde diethylacetal; Hydratropaaldehyde dimethyl acetal; Phenylacetaldehyde glycerol acetal; 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; the aromatic and araliphatic aldehydes such as. B. Benzaldehyde; Phenyl acetaldehyde; 3-phenylpropanal; Hydratropaaldehyde; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; 2-methyl-3- (4-tert-butylphenyl) propanal; 2-methyl-3- (4-isobutylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; Cinnamaldehyde; alpha-butyl cinnamaldehyde; alpha amyl cinnamaldehyde; alpha-hexyl cinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3.4-
Dimethoxybenzaldehyd; 2-Methyl-3-(4-methoxyphenyl)propanal; 2-Methyl-3-(4- methylendioxyphenyl)propanal; der aromatischen und araliphatischen Ketone wie z.B. Acetophenon; 4- Methylacetophenon; 4-Methoxyacetophenon; 4-tert.-Butyl-2,6- dimethylacetophenon; 4-Phenyl-2-butanon; 4-(4-Hydroxyphenyl)-2-butanon; 1 -(2- Naphthalenyl)ethanon;2-Benzofuranylethanon;(3-Methyl-2-benzofuranyl)ethanon; Benzophenon; 1 ,1 ,2,3,3,6-Hexamethyl-5-indanylmethylketon; 6-tert.-Butyl-1 ,1 - dimethyl-4-indanylmethylketon; 1 -[2,3-dihydro-1 ,1 ,2,6-tetramethyl-3-(1 - methylethyl)-1 H-5-indenyl]ethanon; 5',6',7',8'-Tetrahydro-3',5',5',6',8',8'- hexamethyl-2-acetonaphthon; der aromatischen und araliphatischen Carbonsäuren und deren Ester wie z.B. Benzoesäure; Phenylessigsäure; Methylbenzoat; Ethylbenzoat; Hexylbenzoat; Benzyl-benzoat; Methylphenylacetat; Ethylphenylacetat; Geranylphenylacetat; Phenylethyl-phenylacetat; Methylcinnmat; Ethylcinnamat; Benzylcinnamat; Phe- nylethylcinnamat; Cinnamylcinnamat; Allylphenoxyacetat; Methylsalicylat; Isoa- mylsalicylat; Hexylsalicylat; Cyclohexylsalicylat; Cis-3-Hexenylsalicylat; Benzylsa- licylat; Phenylethylsalicylat; Methyl-2,4-dihydroxy-3,6-dimethylbenzoat; Ethyl-3- phenylglycidat; Ethyl-3-methyl-3-phenylglycidat; der stickstoffhaltigen aromatischen Verbindungen wie z.B. 2,4,6-Trinitro-1 ,3- dimethyl-5-tert.-butylbenzol; 3,5-Dinitro-2,6-dimethyl-4-tert.-butylacetophenon; Zimtsäurenitril; 3-Methyl-5-phenyl-2-pentensäurenitril; 3-Methyl-5- phenylpentansäurenitril; Methylanthranilat; Methy-N-methylanthranilat;Dimethoxybenzaldehyde; 2-methyl-3- (4-methoxyphenyl) propanal; 2-methyl-3- (4-methylenedioxyphenyl) propanal; 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-indanyl methyl ketone; 1 - [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1 H-5-indenyl] ethanone; 5 ', 6', 7 ', 8'-tetrahydro-3', 5 ', 5', 6 ', 8', 8'-hexamethyl-2-acetonaphthone; aromatic and araliphatic carboxylic acids and their esters such as benzoic acid; Phenylacetic acid; Methyl benzoate; Ethyl benzoate; Hexyl benzoate; Benzyl benzoate; Methylphenylacetate; Ethylphenylacetate; Geranylphenyl acetate; Phenylethyl phenyl acetate; Methyl cinnmat; Ethyl cinnamate; Benzyl cinnamate; Phenylethyl cinnamate; Cinnamyl cinnamate; Allylphenoxyacetate; Methyl salicylate; Isoamyl salicylate; Hexyl salicylate; Cyclohexyl salicylate; Cis-3-hexenyl salicylate; Benzyl salicylate; Phenylethyl salicylate; Methyl 2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenyl glycidate; Ethyl 3-methyl-3-phenylglycidate; the nitrogen-containing aromatic compounds such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert-butylacetophenone; Cinnamic acid nitrile; 3-methyl-5-phenyl-2-pentenacrylonitrile; 3-methyl-5-phenylpentanoic acid nitrile; Methyl anthranilate; Methyl-N-methylanthranilate;
Schiff'sche Basen von Methylanthranilat mit 7-Hydroxy-3,7-dimethyloctanal, 2- Methyl-3-(4-tert.-butylphenyl)propanal oder 2,4-Dimethyl-3- cyclohexencarbaldehyd; 6-lsopropylchinolin; 6-lsobutylchinolin; 6-sec- Butylchinolin;2-(3-Phenylpropyl)pyridin; Indol; Skatol; 2-Methoxy-3- isopropylpyrazin; 2-lsobutyl-3-methoxypyrazin; der Phenole, Phenylether und Phenylester wie z.B. Estragol; Anethol; Eugenol; Eugenylmethylether; Isoeugenol; Isoeugenylmethylether; Thymol; Carvacrol; Diphenylether; beta-Naphthylmethylether; beta-Naphthylethylether; beta- Naphthylisobutylether; 1 ,4-Dimethoxybenzol; Eugenylacetat; 2-Methoxy-4- methylphenol; 2-Ethoxy-5-(1 -propenyl)phenol; p-Kresylphenylacetat; der heterocyclischen Verbindungen wie z.B. 2,5-Dimethyl-4-hydroxy-2H-furan-3- on; 2-Ethyl-4-hydroxy-5-methyl-2H-furan-3-on; 3-Hydroxy-2-methyl-4H-pyran-4- on; 2-Ethyl-3-hydroxy-4H-pyran-4-on; der Lactone wie z.B. 1 ,4-Octanolid; 3-Methyl-1 ,4-octanolid; 1 ,4-Nonanolid; 1 ,4- Decanolid; 8-Decen-1 ,4-olid; 1 ,4-Undecanolid; 1 ,4-Dodecanolid; 1 ,5-Decanolid;Schiff bases of methylanthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexenecarbaldehyde; 6-isopropylquinoline; 6-isobutylquinoline; 6-sec-butylquinoline; 2- (3-phenylpropyl) pyridine; Indole; Skatole; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine; of phenols, phenyl ethers and phenyl esters such as, for example, estragole; Anethole; Eugenol; Eugenyl methyl ether; Isoeugenol; Isoeugenyl methyl ether; Thymol; Carvacrol; Diphenyl ether; beta-naphthyl methyl ether; beta-naphthyl ethyl ether; beta-naphthyl isobutyl ether; 1,4-dimethoxybenzene; Eugenyl acetate; 2-methoxy-4-methylphenol; 2-ethoxy-5- (1-propenyl) phenol; p-cresylphenylacetate; 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-one; the lactones such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1, 5-decanolide;
1 ,5-Dodecanolid;4-Methyl-1 ,4-decanolid; 1 ,15-Pentadecanolid; eis- und trans-11-1,5-dodecanolide; 4-methyl-1,4-decanolide; 1, 15-pentadecanolide; ice and trans-11-
Pentadecen-1 ,15-olid; eis- und trans-12-Pentadecen-1 ,15-olid; 1 ,16-Pentadecen-1, 15-olide; ice and trans-12-pentadecen-1, 15-olide; 1, 16-
Hexadecanolid; 9-Hexadecen-1 ,16-olid; 10-Oxa-1 ,16-hexadecanolid; 11 -Oxa-Hexadecanolide; 9-hexadecen-1, 16-olide; 10-oxa-1,16-hexadecanolide; 11 -Oxa-
1 ,16-hexadecanolid; 12-Oxa-1 ,16-hexadecanolid; Ethylen-1 ,12-dodecandioat; Ethylen-1 ,13-tridecandioat; Cumarin; 2,3-Dihydrocumarin; Octahydrocumarin. 1, 16-hexadecanolide; 12-oxa-1, 16-hexadecanolide; Ethylene 1, 12-dodecanedioate; Ethylene 1, 13-tridecanedioate; Coumarin; 2,3-dihydrocoumarin; Octahydrocumarin.
In Riech- oder Aromastoffkompositionen beträgt die eingesetzte Menge des 2- Methoxymethylphenols vorzugsweise 0,0001 bis 90 Gew.-%, vorzugsweise 0,01 bis 70 Gew.-% und besonders bevorzugt 0,1 bis 50 Gew.-%, bezogen auf die Gesamtmenge der Riech- oder Aromastoffkomposition. Riech- oder Aromastoffkompositionen, die 2-Methoxymethylphenol enthalten, können in flüssiger Form, unverdünnt oder mit einem Lösungsmittel verdünnt zur Parfümierung oder Aromatisierung eingesetzt werden. Geeignete Lösungsmittel hierfür sind z.B. Ethanol, Isopropanol, Diethylenglycolmonoethyleter, Glycerin, Propylenglycol, 1 ,2-Butylenglycol, Dipropylenglycol, Diethylphtalat, Triethylcitrat, Isopropylmyristat, Triacetin, Pflanzenöle usw. In fragrance or flavoring compositions, the amount of 2-methoxymethylphenol used is preferably 0.0001 to 90% by weight, preferably 0.01 to 70% by weight and particularly preferably 0.1 to 50% by weight, based on the Total amount of the fragrance or flavoring composition. Fragrance or flavoring compositions which contain 2-methoxymethylphenol can be used in liquid form, undiluted or diluted with a solvent for perfuming or aromatizing. Suitable solvents for this are e.g. Ethanol, isopropanol, diethylene glycol monoethyleter, glycerin, propylene glycol, 1, 2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, vegetable oils etc.
Zutaten, mit denen 2-Methoxymethylphenol kombiniert werden kann, sind beispielsweise: Ingredients that can be combined with 2-methoxymethylphenol include:
Konservierungsmittel, Abrasiva, Antiakne-Mittel, Mittel gegen Hautalterung, anitbakterielle Mittel, Anticellulitis-Mittel, Antischuppen-Mittel, entzündungs- hemmende Mittel, irritationsverhindernde Mittel, irritationshemmende Mittel, antimikrobielle Mittel, Antioxidantien, Adstringentien, schweisshemmende Mittel, antiseptische Mittel, Antistatika, Binder, Puffer, Trägermaterialien, Chelatbildnder, Zellstimulantien, reinigende Mittel, pflegende Mittel, Enthaarungsmittel, oberflächenaktive Substanzen, deodorierende Mittel, Antiperspirantien, Weichma- eher, Emulgatoren, Enzyme, ätherische Öle, Fasern, Filmbildner, Fixateure, Schaumbildner, Schaumstabilisatoren, Substanzen zum Verhindern des Schäumens, Schaumbooster, Fungizide, gelierende Mittel, gelbildende Mittel, Haarpflegemittel, Haarverformungsmittel, Haarglättungsmittel, feuchtigkeitsspendende Mittel, anfeuchtende Substanzen, feuchthaltende Substanzen, bleichende Mittel, stärkende Mittel, fleckenentfernende Mittel, optisch aufhellende Mittel, imprägnierende Mittel, schmutzabweisende Mittel, reibungsverringernde Mittel, Gleitmittel, Feuchtigkeitscremes, Salben, Trübungsmittel, plastifizierende Mittel, deckfähige Mittel, Politur, Glanzmittel, Polymere, Pulver, Proteine, rückfettende Mittel, abschleifende Mittel, Slilcone, hautberuhigende Mittel, hautreinigende Mittel, haut- pflegende Mittel, hautheilende Mittel, Hautaufhellungsmittel, hautschützende Mittel, hauterweichende Mittel, kühlende Mittel, hautkühlende Mittel, wärmende Mittel, hautwärmende Mittel, Stabilisatoren, UV-absorbierende Mittel, UV-Filter, Waschmittel, Weichspüler, suspendierende Mittel, Hautbräunungsmittel, Verdickungsmittel, Vitamine, Öle, Wachse, Fette, Phospholipide, gesättigte Fettsäu- ren, ein- oder mehrfach ungesättigte Fettsäuren, α-Hydroxysäuren, Polyhydroxy- fettsäuren, Verflüssiger, Farbstoffe, farbschützende Mittel, Pigmente, Antikorrosi- va, Aromen, Geschmackstoffe, Riechstoffe, Polyole, Tenside (besonders bevorzugte Kombination, siehe oben), Elektrolyte, organische Lösungsmittel oder Silikonderivate. Des weiteren können erfindungsgemäße Riech- oder Aromastoffkompositionen, die 2-Methoxymethylphenol enthalten, an einem Trägerstoff adsorbiert sein, der sowohl für eine feine Verteilung der Riech- oder Aromastoffe im Produkt als auch für eine kontrollierte Freisetzung bei der Anwendung sorgt. Derartige Träger können poröse anorganische Materialien wie Leichtsulfat, Kieselgele, Zeolithe, Gipse, Tone, Tongranulate, Gasbeton usw. oder organische Materialien wie Hölzer, Cellulose-basierende Stoffe, Zucker, Dextrine (z.B. Maltodextrin) oder Kunststoffe wie PVC, Polyvinylacetate oder Polyurethane sein. Die Kombination aus erfindungsgemäßer Komposition und Trägerstoff stellt einen beispielhaften erfindungsgemäßen Artikel dar. Riech- oder Aromastoffkompositionen, die 2-Methoxymethylphenol enthalten, können auch mikroverkapselt, sprühgetrocknet, als Einschluss-Komplexe oder als Extrusions-Produkte (d. h. erfindungsgemäße Produkte) vorliegen und in dieser Form z. B. einem zu parfümierenden oder zu aromatisierenden Produkt hinzugefügt werden. Preservatives, abrasives, anti-acne agents, anti-aging agents, anti-bacterial agents, anti-cellulite agents, anti-dandruff agents, anti-inflammatory agents, anti-irritant agents, anti-irritant agents, antimicrobial agents, antioxidants, astringents, antiperspirant agents, antiseptic agents, antistatic agents , Buffers, carrier materials, chelating agents, cell stimulants, cleaning agents, care agents, depilatory agents, surface-active substances, deodorising agents, antiperspirants, softening agents, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, Foaming agents, foam stabilizers, substances to prevent foaming, foam boosters, fungicides, gelling agents, gelling agents, hair care products, hair shaping agents, hair straightening agents, moisturizing agents, moisturizing substances, moisturizing substances, bleaching agents, strengthening agents, stain-removing agents, optically brightening agents, imprinting agents , dirt-repellent, friction-reducing agents, lubricants, moisturizers, ointments, opacifiers, plasticizers, opacifying agents, polish, gloss agents, polymers, powders, proteins, lipid-replenishing agents, abrasive agents, slilcone, skin-soothing agents, skin-cleaning agents, skin-care agents, skin healing agents, skin lightening agents, skin protecting agents, skin softening agents, cooling agents, skin cooling agents, warming agents, skin warming agents, stabilizers, UV absorbing agents, UV filters, detergents, fabric softeners, suspendi agents, skin tanning agents, thickeners, vitamins, oils, waxes, fats, phospholipids, saturated fatty acids, mono- or polyunsaturated fatty acids, α-hydroxy acids, polyhydroxy fatty acids, plasticizers, dyes, color-protecting agents, pigments, anti-corrosives, Aromas, flavors, fragrances, polyols, surfactants (particularly preferred combination, see above), electrolytes, organic solvents or silicone derivatives. Furthermore, fragrance or flavoring compositions according to the invention which contain 2-methoxymethylphenol can be adsorbed on a carrier which ensures both a fine distribution of the fragrance or flavoring substances 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, cellulose-based substances, sugars, dextrins (eg maltodextrin) or plastics such as PVC, polyvinyl acetates or polyurethanes. The combination of composition and carrier according to the invention represents an exemplary article according to the invention. Fragrance or flavoring compositions which contain 2-methoxymethylphenol can also be microencapsulated, spray-dried, as inclusion complexes or present as extrusion products (ie products according to the invention) and in this form, for. B. a product to be perfumed or flavored.
Gegebenenfalls können die Eigenschaften der derart modifizierten Kompositio- nen durch sog.„Coaten" mit geeigneten Materialien im Hinblick auf eine gezieltere Duftfreisetzung weiter optimiert werden, wozu vorzugsweise wachsartige Kunststoffe wie z.B. Polyvinylalkohol verwendet werden. Die resultierenden Produkte stellen wiederum erfindungsgemäße Produkte dar. If necessary, the properties of the compositions 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 resulting products in turn represent products according to the invention.
Die Mikroverkapselung der erfindungsgemäßen Riech- oder Aromastoffkomposi- tionen zu erfindungsgemäßen Produkte kann beispielsweise durch das sogenannte Koazervationsverfahren mit Hilfe von Kapselmaterialien z.B. aus polyurethanartigen Stoffen oder Weichgelatine, erfolgen. Die sprühgetrockneten Riech- oder Aromastoffkompositionen können beispielsweise durch Sprühtrocknung einer die Riech- oder Aromastoffkomposition enthaltenden Emulsion, bzw. Dispersion hergestellt werden, wobei als Trägerstoffe modifizierte Stärken, Proteine, Dextrin und pflanzliche Gummen verwendet werden können. Einschluss- Komplexe können z.B. durch Eintragen von Dispersionen von der Riech- oder Aromastoffkomposition und Cyclodextrinen oder Harnstoffderivaten in ein geeignetes Lösungsmittel, z.B. Wasser, hergestellt werden. Extrusions-Produkte kön- nen durch Verschmelzen der Riech- oder Aromastoffkompositionen mit einem geeigneten wachsartigen Stoff und durch Extrusion mit nachfolgender Erstarrung, ggf. in einem geeigneten Lösungsmittel, z.B. Isopropanol, erhalten werden. The microencapsulation of the fragrance or flavoring compositions according to the invention to products according to the invention can be carried out, 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 fragrance or flavoring composition can be produced, for example, by spray drying an emulsion or dispersion containing the fragrance or flavoring composition, and modified starches, proteins, dextrin and vegetable gums can be used as carriers. Inclusion complexes can e.g. by adding dispersions of the fragrance or flavoring composition and cyclodextrins or urea derivatives in a suitable solvent, e.g. Water. Extrusion products can be made by fusing the fragrance or flavoring compositions with a suitable wax-like substance and by extrusion with subsequent solidification, if appropriate in a suitable solvent, e.g. Isopropanol can be obtained.
2-Methoxymethylphenol und Riechstoffkompositionen, die 2- Methoxymethylphenol enthalten, können in konzentrierter Form, in Lösungen oder in oben beschriebener modifizierter Form verwendet werden für die Herstellung von erfindungsgemäßen parfümierten Produkten wie z.B. Parfüm-Extraits, Eau de Parfüms, Eau de Toilettes, Rasierwässer, Eau de Colognes, Pre-shave- Produkte, Splash-Colognes und parfümierten Erfrischungstüchern sowie die Parfümierung von sauren, alkalischen und neutralen Reinigungsmitteln, wie z.B. Fußbodenreinigern, Fensterglasreinigern, Geschirrspülmittel, Bad- und Sanitärreinigern, Scheuermilch, festen und flüssigen WC-Reinigern, pulver- und schaumförmigen Teppichreinigern, Textilerfrischern, Bügelhilfen, flüssigen Waschmitteln, pulverförmigen Waschmitteln, Wäschevorbehandlungsmitteln wie Bleichmittel, Einweichmittel und Fleckenentfernern, Wäscheweichspülern, Waschseifen, Waschtabletten, Desinfektionsmitteln, Oberflächendesinfek- tionsmitteln sowie von Luftverbesserern in flüssiger, gelartiger oder auf einem festen Träger aufgebrachter Form, Aerosolsprays, Wachsen und Polituren wie Möbelpolituren, Fußbodenwachsen, Schuhcremes sowie Körperpflegemitteln wie z.B. festen und flüssigen Seifen, Duschgelen, Shampoos, Rasierseifen, Rasierschäumen, Badeölen, kosmetischen Emulsionen vom Öl-in-Wasser-, vom Was- ser-in-ÖI- und vom Wasser-in-ÖI-in-Wasser-Typ wie z.B. Hautcremes- und - lotionen, Gesichtscremes und -lotionen, Sonnenschutzcremes-und -lotionen, After-sun-cremes und -lotionen, Handcremes und -lotionen, Fußcremes und - lotionen, Enthaarungscremes und -lotionen, After-shave-Cremes und -lotionen, Bräunungscremes und -lotionen, Haarpflegeprodukten wie z.B. Haarsprays, Haargelen, festigenden Haarlotionen, Haarspülungen, permanenten und semipermanenten Haarfärbemitteln, Haarverformungsmitteln wie Kaltwellen und Haarglättungsmitteln, Haarwässern, Haarcremes und -lotionen, Deodorantien und Antiperspirantien wie z.B. Achselsprays, Roll-ons, Deosticks, Deocremes, Produkten der dekorativen Kosmetik wie z.B. Lidschatten, Nagellacke, Make-ups, Lippenstifte, Mascara sowie von Kerzen, Lampenölen, Räucherstäbchen, Insektiziden, Repellenten und Treibstoffen. 2-methoxymethylphenol and fragrance compositions which contain 2-methoxymethylphenol can be used in concentrated form, in solutions or in the modified form described above for the production of perfumed products according to the invention, such as, for example, perfume extracts, eau de parfums, 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-shaped carpet cleaners, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents such as bleach, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets, disinfectants, surface disinfectants and air fresheners applied in a liquid, gel-like or aerosol-based form on aerosol sprays and polishes such as furniture polishes, floor waxes, shoe creams and body care products such as solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, cosmetic emulsions from oil-in-water, water-in-oil and water in-oil-in-water type such as skin creams and lotions, face creams and lotions, sun protection 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 es and lotions, hair care products such as hair sprays, hair gels, setting hair lotions, hair rinses, permanent and semi-permanent hair colorants, hair shaping agents such as cold waves and hair straightening agents, hair lotions, hair creams and lotions, deodorants and antiperspirants, such as axillary sprays, deodorant onsoles, as-ax ons, sprays, Decorative cosmetics products such as eyeshadows, nail polishes, make-ups, lipsticks, mascara and candles, lamp oils, incense sticks, insecticides, repellents and fuels.
Das erfindungsgemäß zu verwendende 2-Methoxymethylphenol kann in aromati- sierte oder zu aromatisierende Produkte eingearbeitet werden, insbesondere der Ernährung, der Mundpflege oder dem Genuss dienende Zubereitungen. Der Ernährung oder dem Genuss dienende Zubereitungen sind z.B. Backwaren (z.B. Brot, Trockenkekse, Kuchen, sonstiges Gebäck), Süßwaren (z.B. Schokoladen, Schokoladenriegelprodukte, sonstige Riegelprodukte, Fruchtgummi, Hart- und Weichkaramellen, Kaugummi), alkoholische oder nicht-alkoholische Getränke (z.B. Kaffee, Tee, Wein, weinhaltige Getränke, Bier, bierhaltige Getränke, Liköre, Schnäpse, Weinbrände, fruchthaltige Limonaden, isotonische Getränke, Erfrischungsgetränke, Nektare, Obst- und Gemüsesäfte, Frucht- oder Gemüse- saftzubereitungen), Instantgetränke (z.B. Instant-Kakao-Getränke, Instant-Tee- Getränke, Instant-Kaffeegetränke), Fleischprodukte (z.B. Schinken, Frischwurstoder Rohwurstzubereitungen, gewürzte oder marinierte Frisch- oder Pökelfleischprodukte), Eier oder Eiprodukte (Trockenei, Eiweiß, Eigelb), Getreidepro- dukte (z.B. Frühstückscerealien, Müsliriegel, vorgegarte Fertigreis-Produkte), Milchprodukte (z.B. Milchgetränke, Milcheis, Joghurt, Kefir, Frischkäse, Weichkäse, Hartkäse, Trockenmilchpulver, Molke, Butter, Buttermilch, teilweise oder ganz hydrolisierte Milchprotein-haltige Produkte), Produkte aus Sojaprotein oder anderen Sojabohnen-Fraktionen (z.B. Sojamilch und daraus gefertigte Produkte, Sojalecithin-haltige Zubereitungen, fermentierte Produkte wie Tofu oder Tempe oder daraus gefertigte Produkte, Sojasoßen), Fruchtzubereitungen (z.B. Konfitüren, Fruchteis, Fruchtsoßen, Fruchtfüllungen), Gemüsezubereitungen (z.B. Ketchup, Soßen, Trockengemüse, Tiefkühlgemüse, vorgegarte Gemüse, in Essig eingelegte Gemüse, eingekochte Gemüse), Knabberartikel (z.B. gebackene oder frittierte Kartoffelchips oder Kartoffelteigprodukte, Brotteigprodukte, Extrudate auf Mais- oder Erdnussbasis), Produkte auf Fett- und Ölbasis oder Emulsionen derselben (z.B. Mayonnaise, Remoulade, Dressings, Würzzubereitungen), sonstige Fertiggerichte und Suppen (z.B. Trockensuppen, Instant-Suppen, vorgegarte Suppen), Gewürze, Würzmischungen sowie insbesondere Aufstreuwürzungen (englisch: Seasonings), die beispielsweise im Snackbereich Anwendung finden. Nach Einarbeiten der erfindungsgemäßen Verbindung sind diese Zubereitungen erfindungsgemäße Zubereitungen (als Beispiel erfindungsgemäßer Produkte). The 2-methoxymethylphenol to be used according to the invention can be incorporated into flavored or flavored products, in particular preparations serving for nutrition, oral care or pleasure. Preparations serving nutrition or pleasure are e.g. baked goods (e.g. bread, dry biscuits, cakes, other pastries), confectionery (e.g. chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (e.g. Coffee, tea, wine, wine-based drinks, beer, beer-based drinks, liqueurs, schnapps, brandies, fruit-containing lemonades, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juices juice preparations), instant drinks (e.g. instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (e.g. ham, fresh sausage or raw sausage preparations, seasoned or marinated fresh or pickled meat products), eggs or egg products (dry egg, protein, egg yolk) , Cereal products (e.g. breakfast cereals, granola bars, pre-cooked ready-rice products), dairy products (e.g. milk drinks, milk ice cream, yoghurt, kefir, cream cheese, soft cheese, hard cheese, dry milk powder, whey, butter, buttermilk, partially or completely hydrolyzed milk protein-containing products) , Products made from soy protein or other soybean fractions (e.g. soy milk and products made from it, preparations containing soy lecithin, fermented products such as tofu or tempe or products made from it, soy sauces), fruit preparations (e.g. jams, fruit ice cream, fruit sauces, fruit fillings), vegetable preparations ( e.g. ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked Vegetables, pickled vegetables, boiled vegetables), snacks (e.g. baked or fried potato chips or potato dough products, bread dough products, extrudates based on corn or peanuts), products based on fat and oil or emulsions thereof (e.g. mayonnaise, tartar sauce, dressings, seasoning preparations) , other ready meals and soups (e.g. dry soups, instant soups, pre-cooked soups), spices, seasoning mixes and, in particular, seasonings, which are used, for example, in the snack area. After incorporation of the compound according to the invention, these preparations are preparations according to the invention (as an example of products according to the invention).
Erfindungsgemäße Zubereitungen können z. B. als Halbfertigware oder als Würzmischung vorliegen. Erfindungsgemäße Zubereitungen können insbesondere als Halbfertigware zur Herstellung weiterer der Ernährung oder dem Genuss dienenden Zubereitungen dienen, insbesondere in sprühgetrockneter Form. Erfindungsgemäße Zubereitungen können auch in Form von Kapseln, Tabletten (nichtüberzogene sowie überzogene Tabletten, z.B. magensaftresistente Überzüge), Dragees, Granula- ten, Pellets, Feststoffmischungen, Dispersionen in flüssigen Phasen, als Emulsi- onen, als Pulver, als Lösungen, als Pasten oder als andere schluck- oder kaubare Zubereitungen als Nahrungsergänzungsmittel vorliegen. Preparations according to the invention can, for. B. as a semi-finished product or as a seasoning mix. Preparations according to the invention can serve, in particular, as semi-finished goods for the production of further preparations serving for nutrition or pleasure, in particular in spray-dried form. Preparations according to the invention can also be in the form of capsules, tablets (non-coated and coated tablets, for example enteric coatings), dragées, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsifiers. onen, as powder, as solutions, as pastes or as other swallowable or chewable preparations as food supplements.
Der Mundpflege dienende erfindungsgemäße Zubereitungen sind insbesondere Mund- und/oder Zahnpflegemittel wie Zahnpasten, Zahngele, Zahnpulver, Mundwässer, Kaugummis und andere Mundpflegemittel. Preparations according to the invention used for oral care are, in particular, oral and / or dental care products such as toothpastes, tooth gels, tooth powder, mouthwashes, chewing gums and other oral care products.
Weitere übliche Wirk-, Grund-, Hilfs- und Zusatzstoffe für der Ernährung, der Mundpflege oder dem Genuss dienende erfindungsgemäße Zubereitungen können in Mengen von 5 bis 99,999999 Gew.-%, vorzugsweise 10 bis 80 Gew.-%, bezogen auf das Gesamtgewicht der Zubereitung, enthalten sein. Ferner können die Zubereitungen Wasser in einer Menge bis zu 99,999999 Gew.-%, vorzugsweise 5 bis 80 Gew.-%, bezogen auf das Gesamtgewicht der Zubereitung, aufweisen. Other customary active ingredients, basic substances, auxiliaries and additives for nutrition, oral care or pleasure-making preparations according to the invention can be used in amounts of 5 to 99.999999% by weight, preferably 10 to 80% by weight, based on the Total weight of the preparation. Furthermore, the preparations can contain water in an amount of up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.
Die erfindungsgemäßen Zubereitungen (als Beispiele erfindungsgemäßer Produkte), enthaltend 2-Methoxymethylphenol, werden gemäß einer bevorzugten Ausgestaltung hergestellt, indem das 2-Methoxymethylphenol als Substanz, als Lösung (z.B. in Ethanol, Wasser oder 1 ,2-Propylenglycol) oder in Form eines Gemisches mit einem festen oder flüssigen Trägerstoff (z.B. Maltodextrin, Stärke, Silicagel), sonstigen Aromen oder Aromastoffen und gegebenfalls weiteren Hilfsmitteln und/oder Stabilisatoren (z.B. natürliche oder künstliche Polysacchari- de und/oder Pflanzengummen wie modifizierte Stärken oder Gummi Arabicum) in eine der Ernährung, der Mundpflege oder dem Genuss dienende Basis- Zubereitung eingearbeitet werden. Vorteilhafterweise können als Lösung und/oder Suspension oder Emulsion vorliegende erfindungsgemäße Zubereitungen auch durch Sprühtrocknung in eine feste erfindungsgemäße Zubereitung (Halbfertigware) überführt werden. According to a preferred embodiment, the preparations according to the invention (as examples of products according to the invention) containing 2-methoxymethylphenol are prepared by using the 2-methoxymethylphenol as a substance, as a solution (for example in ethanol, water or 1,2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (e.g. maltodextrin, starch, silica gel), other flavors or flavorings and, if necessary, other auxiliaries and / or stabilizers (e.g. natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic) in a diet , oral care or basic preparation for pleasure. Preparations according to the invention which are present as a solution and / or suspension or emulsion can advantageously also be converted into a solid preparation according to the invention (semi-finished goods) by spray drying.
Die erfindungsgemäßen sprühgetrockneten festen Zubereitungen (als Beispiel erfindungsgemäßer Produkte) sind als Halbfertigwaren besonders gut zur Herstellung von weiteren erfindungsgemäßen Zubereitungen geeignet. In den erfindungsgemäßen sprühgetrockneten festen Zubereitungen sind vorzugsweise 50 bis 95 % Gew.-% Trägerstoffe, insbesondere Maltodextrin und/oder Stärke, 5 bis 40 % Hilfsstoffe, bevorzugt natürliche oder künstliche Polysaccharide und/oder Pflanzengummen wie modifizierte Stärken oder Gummi Arabicum enthalten. The spray-dried solid preparations according to the invention (as an example of products according to the invention) are particularly well suited as semi-finished goods for the production of further preparations according to the invention. The spray-dried solid preparations according to the invention preferably contain 50 to 95% by weight of carriers, in particular maltodextrin and / or starch, 5 to Contain 40% auxiliaries, preferably natural or artificial polysaccharides and / or plant gums such as modified starches or gum arabic.
Gemäß einer weiteren bevorzugten Ausführungsform werden zur Herstellung erfindungsgemäßer Zubereitungen das erfindungsgemäße 2- Methoxymethylphenol und gegebenenfalls andere Bestandteile der erfindungsgemäßen Zubereitung zunächst in Emulsionen, in Liposomen, z.B. ausgehend von Phosphatidylcholin, in Microsphären, in Nanosphären oder auch in Kapseln, Granulaten oder Extrudaten aus einer für Lebens- und Genussmittel geeigneten Matrix, z.B. aus Stärke, Stärkederivaten (z.B. modifizierte Stärke), Cellulose oder Cellulosederivaten (z.B. Hydroxypropylcellulose), anderen Polysacchariden (z.B. Dextrin, Alginat, Curdlan, Carageenan, Chitin, Chitosan, Pullulan), natürlichen Fetten, natürlichen Wachsen (z.B. Bienenwachs, Carnaubawachs), aus Proteinen, z.B. Gelatine oder sonstigen Naturprodukten (z.B. Schellack) eingearbeitet. Dabei können je nach Matrix die Produkte durch Sprühtrocknung, Sprühgranula- tion, Schmelzgranulation, Koazervation, Koagulation, Extrusion, Schmelzextrusi- on, Emulsionsverfahren, Beschichtung (Coating) oder andere geeignete Verkap- selungsverfahren und gegebenenfalls eine geeignete Kombination der vorgenannten Verfahren erhalten werden. In einem weiteren bevorzugten Herstellungsverfahren für eine erfindungsgemäße Zubereitung wird das 2- Methoxymethylphenol zunächst mit einem oder mehreren geeigneten Komplexbildnern, beispielsweise mit Cyclodextrinen oder Cyclodextrinderivaten, bevorzugt α- oder ß-Cyclodextrin, komplexiert und in dieser komplexierten Form eingesetzt. According to a further preferred embodiment, the 2-methoxymethylphenol according to the invention and optionally other constituents of the preparation according to the invention are initially prepared in emulsions, in liposomes, e.g. starting from phosphatidylcholine, in microspheres, in nanospheres or also in capsules, granules or extrudates from a matrix suitable for foodstuffs and luxury foods, e.g. from starch, starch derivatives (e.g. modified starch), cellulose or cellulose derivatives (e.g. hydroxypropyl cellulose), other polysaccharides (e.g. dextrin, alginate, curdlan, carageenan, chitin, chitosan, pullulan), natural fats, natural waxes (e.g. beeswax, carnauba wax) Proteins, e.g. Gelatin or other natural products (e.g. shellac) incorporated. Depending on the matrix, the products can be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating (coating) or other suitable encapsulation processes and, if appropriate, a suitable combination of the aforementioned processes. In a further preferred production process for a preparation according to the invention, the 2-methoxymethylphenol is first complexed with one or more suitable complexing agents, for example with cyclodextrins or cyclodextrin derivatives, preferably α- or β-cyclodextrin, and used in this complexed form.
Besonders bevorzugt ist eine erfindungsgemäße Zubereitung, bei der die Matrix so gewählt ist, dass 2-Methoxymethylphenol verzögert von der Matrix freigegeben werden, so dass eine langanhaltende Wirkung erzielt wird. Besonders bevorzugt ist insoweit eine Fett-, Wachs-, Polysaccharid- oder Proteinmatrix. A preparation according to the invention is particularly preferred in which the matrix is selected such that 2-methoxymethylphenol is released from the matrix with a delay, so that a long-lasting effect is achieved. In this respect, a fat, wax, polysaccharide or protein matrix is particularly preferred.
Als weitere Bestandteile für erfindungsgemäße, der Ernährung oder dem Genuss dienende Zubereitungen können übliche Grund-, Hilfs- und Zusatzstoffe für Nah- rungs- oder Genussmittel verwendet werden, z.B. Wasser, Gemische frischer oder prozessierter, pflanzlicher oder tierischer Grund- oder Rohstoffe (z.B. rohes, gebratenes, getrocknetes, fermentiertes, geräuchertes und/oder gekochtes Fleisch, Knochen, Knorpel, Fisch, Gemüse, Früchte, Kräuter, Nüsse, Gemüseoder Fruchtsäfte oder -pasten oder deren Gemische), verdauliche oder nicht verdauliche Kohlenhydrate (z.B. Saccharose, Maltose, Fructose, Glucose, Dextrine, Amylose, Amylopektin, Inulin, Xylane, Cellulose, Tagatose), Zuckeralkohole (z.B. Sorbit, Erythritol), natürliche oder gehärtete Fette (z.B. Talg, Schmalz, Palmfett, Kokosfett, gehärtetes Pflanzenfett), Öle (z.B. Sonnenblumenöl, Erdnussöl, Maiskeimöl, Olivenöl, Fischöl, Sojaöl, Sesamöl), Fettsäuren oder deren Salze (z.B. Kaliumstearat), proteinogene oder nicht-proteinogene Amino- säuren und verwandte Verbindungen (z.B. gamma-Aminobuttersäure, Taurin), Peptide (z.B. Glutahthion), native oder prozessierte Proteine (z.B. Gelatine), Enzyme (z.B. Peptidasen), Nukleinsäuren, Nucleotide, Geschmackskorrigenzien für unangenehme Geschmackseindrücke, weitere Geschmacksmodulatoren für weitere, in der Regel nicht unangenehme Geschmackseindrücke, andere ge- schmacksmodulierende Stoffe (z.B. Inositolphosphat, Nucleotide wie Guanosin- monophosphat, Adenosinmonophosphat oder andere Stoffe wie Natriumglutamat oder 2-Phenoxypropionsäure), Emulgatoren (z.B. Lecithine, Diacylglycerole, Gummi arabicum), Stabilisatoren (z.B. Carageenan, Alginat), Konservierungsstoffe (z.B. Benzoesäure, Sorbinsäure), Antioxidantien (z.B. Tocopherol, Ascorbin- säure), Chelatoren (z.B. Citronensäure), organische oder anorganische Säuerungsmittel (z.B. Äpfelsäure, Essigsäure, Citronensäure, Weinsäure, Phosphorsäure), Bitterstoffe (z.B. Chinin, Coffein, Limonin, Amarogentin, Humolone, Lupo- lone, Catechine, Tannine), mineralische Salze (z.B. Natriumchlorid, Kaliumchlorid, Magnesiumchlorid, Natriumphosphate), die enzymatische Bräunung verhin- dernde Stoffe (z.B. Sulfit, Ascorbinsäure), etherische Öle, Pflanzenextrakte, natürliche oder synthetische Farbstoffe oder Farbpigmente (z.B. Carotinoide, Flavonoide, Anthocyane, Chlorophyll und deren Derivate), Gewürze, trigeminal wirksame Stoffe oder Pflanzenextrakte, enthaltend solche trigeminal wirksamen Stoffe, synthetische, natürliche oder naturidentische Aromastoffe oder Riech- stoffe sowie Geruchskorrigentien. The usual constituents, auxiliaries and additives for foodstuffs or luxury foods, for example water, mixtures of fresh or processed vegetable or animal raw materials or raw materials (for example raw materials) can be used as further constituents for preparations according to the invention which are used for nutrition or pleasure , roasted, dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetables or fruit juices or pastes or their mixtures), digestible or non-digestible carbohydrates (e.g. sucrose, maltose, fructose, Glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose), sugar alcohols (e.g. sorbitol, erythritol), natural or hardened fats (e.g. tallow, lard, palm fat, coconut fat, hardened vegetable fat), oils (e.g. sunflower oil, peanut oil, Corn oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or their salts (eg potassium stearate), proteinogenic or non-proteinogenic amino acids and related compounds (eg gamma-aminobutyric acid, taurine), peptides (eg glutahthione), native or processed proteins (eg gelatin), enzymes (eg peptidases), nucleic acids, nucleotides, taste corrections for unpleasant taste impressions, further taste modulators for further, generally not unpleasant taste impressions, other taste-modulating substances (e.g. inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), emulsifiers (e.g. lecithins, diacylglycerols, gum arabic), stabilizers, e.g. caramelizing agents Alginate), preservatives (e.g. benzoic acid, sorbic acid), antioxidants (e.g. tocopherol, ascorbic acid), chelators (e.g. citric acid), organic or inorganic acidulants (e.g. malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid), bitter substances (e.g. quinine, caffeine) , Limonin, Amarogentin, Humolone, Lupolone, Catechine, Tannins), mineral salts (eg sodium chloride, potassium chloride, magnesium chloride, sodium phosphate), substances that prevent enzymatic browning (eg sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or color pigments (e.g. carotenoids, flavonoids, anthoc yane, chlorophyll and their derivatives), spices, trigeminally active substances or plant extracts, containing such trigeminally active substances, synthetic, natural or nature-identical flavorings or fragrances and odor correctors.
Zahnpflegemittel (als Basis für der Mundpflege dienende Zubereitungen), die 2- Methoxymethylphenol enthalten, umfassen im Allgemeinen ein abrasives System (Schleif- oder Poliermittel), wie z.B. Kieselsäuren, Calciumcarbonate, Calcium- phosphate, Alumiuniumoxide und/oder Hydroxylapatite, oberflächenaktive Substanzen wie z.B. Natriumlaurylsulfat, Natriumlaurylsarcosinat und/oder Cocami- dopropylbetain, Feuchthaltemitteln wie z.B. Glycerin und/oder Sorbit, Verdi- ckungsmittel, wie z.B. Carboxymethylcellulose, Polyethylenglycole, Carrageenan und/oder Laponite®, Süßstoffe, wie z.B. Saccharin, Geschmackskorrigenzien für unangenehme Geschmackseindrücke, Geschmackskorrigenzien für weitere, in der Regel nicht unangenehme Geschmackseindrücke, geschmacksmodulierende Stoffe (z.B. Inositolphosphat, Nucleotide wie Guanosinmonophosphat, Adeno- sinmonophosphat oder andere Stoffe wie Natriumglutamat oder 2-Phen- oxypropionsäure), Kühlwirkstoffen wie z.B. Menthol, Mentholderivate (z.B. L- Menthol, L-Menthyllactat, L-Menthylalkylcarbonate, Menthonketale, Menthancar- bonsäureamide), 2,2,2-Trialkylessigsäureamiden (z.B. 2,2-Dental care products (which are used as the basis for oral care preparations) and which contain 2-methoxymethylphenol generally comprise an abrasive system (Grinding or polishing agents), such as, for example, silicas, calcium carbonates, calcium phosphates, aluminum oxides and / or hydroxylapatites, surface-active substances such as, for example, sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine, humectants such as, for example, glycerol and / or sorbitol, thickeners, such as carboxymethyl cellulose, polyethylene glycols, carrageenan and / or Laponite ® , sweeteners such as saccharin, taste corrections for unpleasant taste impressions, taste corrections for other, usually not unpleasant taste impressions, taste-modulating substances (eg inositol phosphate, nucleotides such as guanosine monophone) Substances such as sodium glutamate or 2-phenoxypropionic acid), cooling agents such as menthol, menthol derivatives (e.g. L-menthol, L-menthyl lactate, L-menthyl alkyl carbonates, menthone ketals, menthane carboxamides), 2,2,2-trialkyl acetic acid amides (e.g. 2.2 -
Diisopropylpropionsäuremethylamid), Icilin und Icilin-Derivate, Stabilisatoren und aktive Wirkstoffe, wie z.B. Natriumfluorid, Natriummonofluorphosphat, Zinndifluo- rid, quartären Ammoniumfluoriden, Zinkeitrat, Zinksulfat, Zinnpyrophosphat, Zinndichlorid, Mischungen verschiedener Pyrophosphate, Triclosan, Cetylpyridi- niumchlorid, Aluminiumlactat, Kaliumeitrat, Kaliumnitrat, Kaliumchlorid, Strontiumchlorid, Wasserstoffperoxid, Aromen und/oder Natriumbicarbonat oder Ge- ruchskorrigentien. Diisopropylpropionic acid methylamide), cilin and cilin derivatives, stabilizers and active ingredients, such as e.g. Sodium fluoride, sodium monofluorophosphate, Zinndifluo- chloride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures niumchlorid various pyrophosphates, triclosan, Cetylpyridi- ruchskorrigentien, aluminum lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavors and / or sodium bicarbonate or overall .
Kaugummis (als weiteres Beispiel für der Mundpflege dienende Zubereitungen), welche 2-Methoxymethylphenol enthalten, umfassen im allgemeinen eine Kaugummibase, d.h. eine beim Kauen plastisch werdende Kaumasse, Zucker verschiedener Arten, Zuckeraustauschstoffe, andere süß schmeckende Stoffe, Zuckeralkoholen, Geschmackskorrigenzien für unangenehme Geschmackseindrücke, andere Geschmacksmodulatoren für weitere, in der Regel nicht unangenehme Geschmackseindrücke, geschmacksmodulierende Stoffe (z.B. Inositolphosphat, Nucleotide wie Guanosinmonophosphat, Adenosinmonophosphat oder andere Stoffe wie Natriumglutamat oder 2-Phenoxypropionsäure), Feucht- haltemittel, Verdicker, Emulgatoren, Aromen und Stabilisatoren oder Geruchskor- rigentien. Bevorzugt können die erfindungsgemäßen Zubereitungen auch neben der erfindungsgemäß einzusetzenden Verbindung eine (zusätzliche) Aromakomposition enthalten, um den Geschmack und/oder Geruch der Zubereitung abzurunden und zu verfeinern. Geeignete (zusätzliche) Aromakompositionen enthalten z.B. synthetische, natürliche oder naturidentische Aroma-, Riech- und Geschmacksstoffe sowie geeignete Hilfs- und Trägerstoffe. Chewing gums (as another example of preparations used for oral care) which contain 2-methoxymethylphenol generally comprise a chewing gum base, ie a chewing gum which becomes plastic when chewed, sugars of various types, sugar substitutes, other sweet-tasting substances, sugar alcohols, taste corrections for unpleasant taste impressions, other taste modulators for other, usually not unpleasant, taste impressions, taste-modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), moisturizers, thickeners, emulsifiers, flavors and stabilizers or odors. In addition to the compound to be used according to the invention, the preparations according to the invention can preferably also contain an (additional) aroma composition in order to round off and refine the taste and / or smell of the preparation. Suitable (additional) aroma compositions contain, for example, synthetic, natural or nature-identical aromas, fragrances and flavors as well as suitable auxiliaries and carriers.
Die folgenden Beispiele erläutern die Erfindung; sofern nicht anders angegeben beziehen sich Anteile und Prozente auf das Gewicht. The following examples illustrate the invention; unless otherwise stated, parts and percentages are by weight.
Beispiel 1 : Darstellung von 2-Methoxymethylphenol 1.1. Darstellung von Salicylalkohol: Example 1: Preparation of 2-methoxymethylphenol 1.1. Preparation of salicylic alcohol:
In einem 4 I Rührwerk wurden 2200 g Wasser und 200 g (3 mol) Kaliumhydroxid 85% vorgelegt und anschließend ohne Kühlung (exotherme Reaktion) 366 g (3 mol) Salicylaldehyd dazugegeben. Anschließend wurden in 4-5 Portionen 30 g (0,78 mol) Natriumboranat hinzugefügt. Nach beendeter Reaktion (DC-Kontrolle, Hexan/Ether 2:1 ) wurde mit 375 g (1 ,96 mol) Schwefelsäure 50% angesäuert und der ausgefallene Salicylalkohol abgesaugt. 2200 g of water and 200 g (3 mol) of potassium hydroxide 85% were placed in a 4 l stirrer and then 366 g (3 mol) of salicylaldehyde were added without cooling (exothermic reaction). Then 30 g (0.78 mol) of sodium boranate were added in 4-5 portions. After the reaction had ended (TLC control, hexane / ether 2: 1), 50% acidified with 375 g (1.96 mol) of sulfuric acid and the precipitated salicyl alcohol was filtered off with suction.
Rohausbeute: 420 g (feucht). Raw yield: 420 g (moist).
1.2. Darstellung von 2-Methoxymethylphenol: 1.2. Preparation of 2-methoxymethylphenol:
Ein Gemisch aus 2200 ml Methanol, 50 g Schwefelsäure 50 % und 420 g Salicy- lalkohol roh (aus Beispiel 1.1 ) wurde 2 h unter Rückfluß erhitzt. Anschließend wurde mit einem Gemisch aus 50 g Natriumhydrogencarbonat und 100 g Wasser neutralisiert. Das Methanol wurde am Rotationsverdampfer abgezogen und der Rückstand mit ca. 1000 g Wasser und 200 g Ether aufgenommen. Die organische Phase wurde abgetrennt, mit Wasser gewaschen und das Lösungsmittel abgezogen. Der Rückstand (250 g) wurde anschließend an einer Claisenkolonne fraktioniert. A mixture of 2200 ml of methanol, 50 g of 50% sulfuric acid and 420 g of crude salicylic alcohol (from Example 1.1) was heated under reflux for 2 h. The mixture was then neutralized with a mixture of 50 g of sodium hydrogen carbonate and 100 g of water. The methanol was removed on a rotary evaporator and the residue was taken up in about 1000 g of water and 200 g of ether. The organic phase was separated off, washed with water and the solvent was stripped off. The residue (250 g) was then fractionated on a Claisen column.
Ausbeute: 148 g (37 % über beide Stufen) Sdp.: 70°C/2 mbar Yield: 148 g (37% over both stages) Sp: 70 ° C / 2 mbar
1H-NMR (CDCI3, TMS, 400 MHz): δ = 3.43 (s, 3H), 4.65 (s, 2H), 6.84 (ddd, J = 7.4, 7.4, 1.2 Hz, 1 H), 6.88 (dddt, J = 8.1 , 1.2, 0.4, 0.4 Hz, 1 H), 7.01 (ddm, J = 7.5, 1.7 Hz, 1 H), 7.20 (dddt, J = QA , 7.3, 1.7, 0.4 Hz, 1 H), 7.49 (s, OH). 13C-NMR (CDCI3, TMS, 100 MHz): δ = 58.2 (q), 74.0 (t), 116.4 (d), 119.9 (d), 122.1 (s), 128.2 (d), 129.5 (d), 156.2 (s). 1 H-NMR (CDCI 3 , TMS, 400 MHz): δ = 3.43 (s, 3H), 4.65 (s, 2H), 6.84 (ddd, J = 7.4, 7.4, 1.2 Hz, 1 H), 6.88 (dddt , J = 8.1, 1.2, 0.4, 0.4 Hz, 1 H), 7.01 (ddm, J = 7.5, 1.7 Hz, 1 H), 7.20 (dddt, J = QA, 7.3, 1.7, 0.4 Hz, 1 H), 7.49 (s, OH). 13 C-NMR (CDCI 3 , TMS, 100 MHz): δ = 58.2 (q), 74.0 (t), 116.4 (d), 119.9 (d), 122.1 (s), 128.2 (d), 129.5 (d) , 156.2 (s).
Beispiel 2: Parfümkomposition (Riechstoffkomposition) Example 2: Perfume composition (fragrance composition)
GewichtsteileParts by weight
Aldehyd C6 2,0 Aldehyde C6 2.0
Aldehyd C14 sog. (gamma-Undecalacton) 2,0  Aldehyde C14 so-called (gamma-undecalactone) 2.0
Aldehyd C16 sog. (Ethyl-3-methyl-3-phenylglycidate) 26,0  Aldehyde C16 so-called (ethyl-3-methyl-3-phenylglycidate) 26.0
Benzaldehyd, 10% in DPG 5,0  Benzaldehyde, 10% in DPG 5.0
Butylacetat 0,1  Butyl acetate 0.1
Citronellol 0,3  Citronellol 0.3
Damascenon 1 ,1  Damascenon 1, 1st
Damascone delta 2,0  Damascone delta 2.0
Decalacton delta 4,0  Decalactone delta 4.0
Decalacton gamma 2,0  Decalactone gamma 2.0
Essigsäure 1.5  Acetic acid 1.5
Ethylbenzoat 1 ,0  Ethyl benzoate 1.0
Ethylcapronat 10,2  Ethyl capronate 10.2
Ethylmaltol 8,0  Ethyl maltol 8.0
Ethylpropionat 0,4  Ethyl propionate 0.4
Ethylsalicylat 0,1  Ethyl salicylate 0.1
Ethylvanillin, 10% in DPG 8,0  Ethyl vanillin, 10% in DPG 8.0
Frambinon (4-(4-Hydroxyphenyl)-butan-2-on) 12,0  Frambinone (4- (4-hydroxyphenyl) butan-2-one) 12.0
Frambinonmethylether (4-(4-Methoxy-phenyl)-butan-2-on) 8,0  Frambinone methyl ether (4- (4-methoxyphenyl) butan-2-one) 8.0
Geraniol 1.0  Geraniol 1.0
Hexenal trans-2 0,1  Hexenal trans-2 0.1
Hexenol cis-3 56,0  Hexenol cis-3 56.0
Hexenylacetat cis,trans-3 4,6  Hexenyl acetate cis, trans-3 4.6
Hexenylacetat cis-3 5,0  Hexenyl acetate cis-3 5.0
Hexenylformiat cis,trans-3 0,3  Hexenyl formate cis, trans-3 0.3
Hexylacetat 2,5  Hexyl acetate 2.5
lonon alpha 48,0 lonon alpha 48.0
lonon beta 21 ,3  lonon beta 21, 3
Isoamylacetat, 10% in DPG 4,0 lsoamylbutyrat 2,0Isoamyl acetate, 10% in DPG 4.0 isoamyl butyrate 2.0
Isobutylacetat 4,2 Isobutyl acetate 4.2
Isoeugenolmethylether 18,0  Isoeugenol methyl ether 18.0
Menthol L 8,0  Menthol L 8.0
Methylacetophenon para 0,1  Methyl acetophenone para 0.1
Methylcinnamat 26,0  Methyl cinnamate 26.0
Octylacetat-1 0,1  Octylacetate-1 0.1
Parmanyl® (3-[((Z)-Hex-3-enyl)oxy]-propionitril) 4Parmanyl ® (3 - [((Z) -hex-3-enyl) oxy] -propionitrile) 4
Phenylethylacetat 0,1  Phenylethyl acetate 0.1
Phenylethylalkohol 2,0  Phenylethyl alcohol 2.0
Propionsäure 1.0  Propionic acid 1.0
Rosaphen (2-Methyl-5-phenylpentanol) 43,0  Rosaphen (2-methyl-5-phenylpentanol) 43.0
Strawberiff, 10% in DPG (2-Methyl-2-pentansäure) 2,0  Strawberiff, 10% in DPG (2-methyl-2-pentanoic acid) 2.0
Styrolylpropionat 14,0  Styrolyl propionate 14.0
Terpineol rein 16,0  Terpineol pure 16.0
Dipropylenglycol 623,0  Dipropylene glycol 623.0
Verwendete Abkürzungen: DPG = Dipropylenglycol Abbreviations used: DPG = dipropylene glycol
Geruchsbeschreibung der Riechstoffkomposition ohne 2-Methoxymethylphenol: frisch, fruchtig, Himbeere, vanillig Nach Meinung der Parfümeure bekommt diese Riechstoffkomposition durch den Zusatz von 5 Teilen 2-Methoxymethylphenol eine schwach ausgeprägte vanillige, nelkige und ledrige Note. Der Eindruck von Frische und Fruchtigkeit (hier speziell der ,,Himbeer"-Charakter) wird durch den Zusatz von 2-Methoxymethylphenol erheblich verstärkt, d.h. dass 2-Methoxymethylphenol insoweit als „Booster" wirkt. 2-Methoxymethylphenol fügt sich gut in die Komposition ein und gibt der Komposition mehr Glanz, rundet diese ab und verleiht ihr mehr Harmonie sowie Natürlichkeit. Ferner machte sich in der 2-Methoxymethylphenol enthaltenden Riechstoffkomposition die stark fixierende Wirkung des 2-Methoxymethylphenols bemerkbar. Beispiel 3: Sensorische Vergleichsdaten Description of the smell of the fragrance composition without 2-methoxymethylphenol: fresh, fruity, raspberry, vanilla In the opinion of the perfumers, the addition of 5 parts of 2-methoxymethylphenol gives this fragrance composition a slightly pronounced vanilla, carnation and leathery note. The impression of freshness and fruitiness (here especially the "raspberry" character) is considerably enhanced by the addition of 2-methoxymethylphenol, ie that 2-methoxymethylphenol acts as a "booster". 2-methoxymethylphenol fits well into the composition and gives the composition more shine, rounds it off and gives it more harmony and naturalness. The strong fixative effect of 2-methoxymethylphenol was also noticeable in the fragrance composition containing 2-methoxymethylphenol. Example 3: Sensory comparison data
Tabelle 3 zeigt einige ausgewählte sensorische Daten, die das sensorische Potential von 2-Methoxymethylphenol verdeutlichen. Als Vergleich diente Isobu- tylchinolin der folgenden Formel:
Figure imgf000040_0001
Table 3 shows some selected sensory data that illustrate the sensory potential of 2-methoxymethylphenol. Isobutylquinoline of the following formula was used for comparison:
Figure imgf000040_0001
Geruchsbeschreibung des Isobutylchinolins: Eichenmoos (oakmoss), würzig, erdig Description of the smell of isobutylquinoline: oakmoss, spicy, earthy
Die Vergleichssubstanz Isobutylchinolin wurde hier nicht wegen ihres Eigengeruchs ausgewählt, sondern vielmehr wegen ihrer Eigenschaft als "Booster" zu wirken (vgl. insoweit Arctander, in Perfume and Flavor Chemicals, wie oben zitiert, "... the effect is more that of a general "lift" than actually an odor contributi- on, and the quinoline odor should not be part of the fragrance picture, but should appear with an undetectable note of radiation and strength."). The comparative substance isobutylquinoline was not selected here because of its own smell, but rather because of its property as a "booster" (cf. Insofar Arctander, in Perfume and Flavor Chemicals, as quoted above, "... the effect is more that of a general "lift" than actually an odor contribution, and the quinoline odor should not be part of the fragrance picture, but should appear with an undetectable note of radiation and strength. ").
Tabelle 3: Sensorische Daten von 2-Methoxymethylphenol im direkten Vergleich zu Isobutylchinolin Table 3: Sensory data of 2-methoxymethylphenol in direct comparison to isobutylquinoline
Figure imgf000040_0002
Figure imgf000041_0001
Figure imgf000040_0002
Figure imgf000041_0001
Beispiel 4: Stabilität des 2-Methoxymethylphenols in tensidhaltigen Produkten Example 4: Stability of 2-methoxymethylphenol in surfactant-containing products
In Tabelle 4 ist die Stabilität des 2-Methoxymethylphenols in unterschiedlichen (tensidhaltigen) Produkten anhand der analytischen Wiederfindungsraten darge- stellt. Table 4 shows the stability of 2-methoxymethylphenol in different (surfactant-containing) products based on the analytical recovery rates.
Tabelle 4: Wiederfindungsraten an 2-Methoxymethylphenol (Lagerung bei 38°C, Angaben in Gew.-%): Table 4: Recovery rates on 2-methoxymethylphenol (storage at 38 ° C, data in% by weight):
Figure imgf000041_0002
Figure imgf000041_0002
Beispiel 5: Shampoo Example 5: Shampoo
2-Methoxymethylphenol wurde als 50 Gew.%-ige Lösung in Diethylphthalat bereitgestellt, welche in einer Dosierung von 0,2 Gew.-% in eine Shampoo - Grundmasse der folgenden Rezeptur eingearbeitet wurde: Natriumlaurylethersulfat 12% 2-methoxymethylphenol was provided as a 50% by weight solution in diethyl phthalate, which was incorporated in a dosage of 0.2% by weight into a shampoo base composition of the following formulation: Sodium lauryl ether sulfate 12%
(z.B. Texapon NSO, Fa. Cognis Deutschland GmbH) (e.g. Texapon NSO, Cognis Deutschland GmbH)
Cocamidopropylbetain 2%  Cocamidopropyl betaine 2%
(z.B. Dehyton K, Fa. Cognis Deutschland GmbH) (e.g. Dehyton K, Cognis Deutschland GmbH)
Natriumchlorid 1 ,4% Sodium chloride 1.4%
Citronensäure 1 ,3%  Citric acid 1.3%
Phenoxyethanol, Methyl-, Ethyl-, Butyl-, Phenoxyethanol, methyl, ethyl, butyl,
und Propylparaben 0,5% and propylparaben 0.5%
Pfirsichriechstoffmischung umfasend gamma-Undecalacton 0,5% Peach fragrance mixture comprising gamma undecalactone 0.5%
Wasser 82,3% Water 82.3%
Der pH-Wert der Shampoo-Grundmasse lag bei etwa 6. Hieraus wurden 100 ml_ einer 20 Gew.%-igen wässrigen Shampoo-Lösung hergestellt. In dieser Sham- poo-Lösung wurden 2 Haarsträhnchen gemeinsam für 2 Minuten gewaschen und anschließend 20 Sekunden unter fließendem handwarmen Wasser gespült. Eine Haarsträhne wurde nass in Aluminiumfolie eingepackt und die zweite Haarsträhne mit einem Fön getrocknet. Beide Haarsträhnen wurden von einem Panel geruchlich beurteilt. Beide Haarsträhnen zeigten einen frischen, pfirsich- fruchtigen und süßen Geruch, wobei der Gesamteindruck strahlend, abgerundet, natürlich und harmonisch empfunden wurde. The pH of the shampoo base was around 6. From this, 100 ml of a 20% by weight aqueous shampoo solution were produced. In this shampoo solution, 2 strands of hair were washed together for 2 minutes and then rinsed under running, lukewarm water for 20 seconds. One strand of hair was wrapped wet in aluminum foil and the second strand of hair was dried with a hair dryer. Both strands of hair were assessed in terms of smell by a panel. Both strands of hair showed a fresh, peach-fruity and sweet smell, whereby the overall impression was radiant, rounded, natural and harmonious.
Beispiel 6: Weichspüler Example 6: Fabric softener
Die Parfümölkomposition aus Beispiel 2 (nach Zusatz von 2- Methoxymethylphenol) wurde in einer Dosierung von 0,5 Gew.-% in eine Weich- spüler-Grundmasse folgender Zusammensetzung eingearbeitet: Quarternäres Ammoniummethosulfat (Esterquat), ca. 90% 5,5% (z.B. Rewoquat WE 18, Fa. Witco Surfactants GmbH) The perfume oil composition from Example 2 (after the addition of 2-methoxymethylphenol) was incorporated in a dosage of 0.5% by weight into a fabric softener base of the following composition: Quaternary ammonium methosulfate (ester quat), approx. 90% 5.5% (e.g. Rewoquat WE 18, Witco Surfactants GmbH)
Alkyldimethylbenzylammoniumchlorid, ca. 50% 0,2% Alkyldimethylbenzylammonium chloride, approx. 50% 0.2%
(z.B. Preventol R50, Fa. Bayer AG) Farblösung, ca. 1 %-ig 0,3% Wasser 94,0% (e.g. Preventol R50, Bayer AG) Color solution, approx. 1% 0.3% water 94.0%
Der pH-Wert des Weichspüler-Grundmasse lag im Bereich 2 - 3. Zwei Stofflappen wurden mit 370 g einer 1 %-igen wässrigen Weichspüler-Lösung in einer Linetest-Maschine im Weichspülprogramm 30 Minuten bei 20°C gespült. Die Lappen wurden ausgewrungen und anschließend 20 Sekunden geschleudert. Ein Lappen wurde nass eingeschweißt, und einer zum Trocknen aufgehängt. Anschließend wurden beide Lappen durch ein Panel geruchlich beurteilt. Beide Lappen zeigten einen frischen, himbeer-fruchtigen und vanillig-süßlichen Geruch mit schwachen ledrig-nelkigen Aspekten, wobei der Gesamteindruck strahlend, abgerundet, natürlich und harmonisch empfunden wurde. The pH of the fabric softener base was in the range 2 - 3. Two cloths were rinsed with 370 g of a 1% aqueous fabric softener solution in a Linetest machine in the fabric softener program for 30 minutes at 20 ° C. The rags were wrung out and then flung for 20 seconds. A rag was welded wet and one hung up to dry. Subsequently, both cloths were assessed for odor by a panel. Both rags showed a fresh, raspberry-fruity and vanilla-sweet smell with weak leathery-clove-like aspects, whereby the overall impression was radiant, rounded, natural and harmonious.
Beispiel 7: Waschpulver Example 7: Washing powder
Die Parfümölkomposition aus Beispiel 2 (nach Zusatz von 2- Methoxymethylphenol) wurde in einer Dosierung von 0,3 Gew.-% in eine Waschpulver-Grundmasse der folgenden Rezeptur eingearbeitet: The perfume oil composition from Example 2 (after the addition of 2-methoxymethylphenol) was incorporated in a dosage of 0.3% by weight into a washing powder base composition of the following recipe:
Lineares Na-Alkylbenzolsulfonat 8,8 % Linear Na alkylbenzenesulfonate 8.8%
Ethoxylierter Fettalkohol C12-18 (7 EO) 4,7 %  Ethoxylated fatty alcohol C12-18 (7 EO) 4.7%
Na-Seife 3,2 %  Na soap 3.2%
Entschäumer  Defoamer
DOW CORNING(R) 2-4248S DOW CORNING (R) 2-4248S
POWDERED ANTIFOAM, Silikonöl auf Zeolith als Trägermaterial 3,9 % POWDERED ANTIFOAM, Silicon oil on zeolite as carrier material 3.9%
Zeolith 4A 28,3 %  Zeolite 4A 28.3%
Na-Carbonat 1 1 ,6 %  Na carbonate 1 1.6%
Na-SaIz eines Copolymers aus Acryl- und Maleinsäure (Sokalan CP5) 2,4 %  Na salt of a copolymer of acrylic and maleic acid (Sokalan CP5) 2.4%
Na-Silicat 3,0 %  Na silicate 3.0%
Carboxymethylzellulose 1 ,2 %  Carboxymethyl cellulose 1, 2%
Dequest 2066 2,8 %  Dequest 2066 2.8%
([[(Phosphonomethyl)imino]bis[(ethylennitrilo)bis  ([[(Phosphonomethyl) imino] to [(ethylene nitrile) to
(methylen)]]tetrakis-phosphonsäure, Natriumsalz)  (methylene)]] tetrakis-phosphonic acid, sodium salt)
Optischer Aufheller 0,2 %  Optical brightener 0.2%
Na-Sulfat 6,5 %  Na sulfate 6.5%
Protease 0,4 %  Protease 0.4%
Natriumperborattetrahydrat 21 ,7 %  Sodium perborate tetrahydrate 21.7%
Riechstoffkomposition mit Rosengeruch 0,3 %  Fragrance composition with a smell of rose 0.3%
TAED 1 ,0 %  TAED 1.0%
Zwei Stofflappen wurden mit 370 g einer 1 %-igen wässrigen Waschpulverlauge (der pH-Wert der Waschpulverlauge liegt deutlich im basischen Bereich) in einer Linetest-Maschine im Hauptwaschgang 45 Minuten bei 60°C gewaschen. Die Lappen wurden zunächst 5 Minuten mit kaltem Wasser gespült, ausgewrungen und anschließend 20 Sekunden geschleudert. Ein Lappen wurde nass eingeschweißt, und einer zum Trocknen aufgehängt. Anschließend wurden beide Lappen durch ein Panel geruchlich beurteilt. Beide Lappen zeigten einen frischen, rosig-blumigen, himbeer-fruchtigen und leicht vanillig-süßlichen Geruch, wobei der Gesamteindruck glänzend, abgerundet und harmonisch empfunden wurde. Beispiel 8: Deo-Stick Two cloths were washed with 370 g of a 1% aqueous washing powder solution (the pH value of the washing powder solution is clearly in the basic range) in a Linetest machine in the main wash cycle at 60 ° C for 45 minutes. The rags were first rinsed with cold water for 5 minutes, wrung out and then spun for 20 seconds. A rag was welded wet and one hung up to dry. Subsequently, both cloths were assessed for odor by a panel. Both rags showed a fresh, rosy-flowery, raspberry-fruity and slightly vanilla-sweet smell, whereby the overall impression was shiny, rounded and harmonious. Example 8: Deodorant stick
Die Parfümölkomposition aus Beispiel 2 (nach Zusatz von 2- Methoxymethylphenol) wurde in einer Dosierung von 0,25 Gew.-% in eine Deo- Stick-Grundmasse der folgenden Rezeptur eingearbeitet: The perfume oil composition from Example 2 (after the addition of 2-methoxymethylphenol) was incorporated in a dosage of 0.25% by weight into a deodorant base composition of the following recipe:
Figure imgf000045_0001
Figure imgf000045_0001
Der Geruch des Deo-Sticks selbst sowie der in der Nähe der Achselhöhle wahrnehmbare Geruch nach Anwendung des Deo-Sticks zeigten einen frischen, himbeer-fruchtigen und vanillig-süßlichen Geruch mit schwachen ledrig-nelkigen Aspekten, wobei der Gesamteindruck strahlend, abgerundet, natürlich und harmonisch empfunden wurde. The smell of the deodorant stick itself, as well as the smell after using the deodorant stick, which was perceptible near the armpit, showed a fresh, raspberry-fruity and vanilla-sweet smell with weak leathery-clove-like aspects, the overall impression being radiant, rounded, natural and was felt harmoniously.

Claims

Patentansprüche Claims
1. Verwendung von 2-Methoxymethylphenol als Riech- oder Aromastoff mit einer vanilligen, nelkigen und/oder ledrigen Note. 1. Use of 2-methoxymethylphenol as a fragrance or aroma substance with a vanilla, carnation and / or leathery note.
2. Verwendung von 2-Methoxymethylphenol als Booster für Riech- oder Aroma Stoffe. 2. Use of 2-methoxymethylphenol as a booster for odoriferous or aromatic substances.
3. Verfahren zum Vermitteln, Modifizieren und/oder Verstärken (Boosten) eines Geruchs oder Geschmacks mit einer, mehreren oder sämtlichen der Noten vanillig, nelkig und/oder ledrig, wobei eine Menge 2-Methoxymethylphenol oder einer 2-Methoxymethylphenol umfassenden Riech- oder Aromastoffkomposition mit einem Erzeugnis in Kontakt gebracht oder gemischt wird. 3. A method of imparting, modifying and / or enhancing (boosting) an odor or taste with one, several or all of the notes vanilla, clove-like and / or leathery, wherein a quantity of 2-methoxymethylphenol or a 2-methoxymethylphenol composition comprising an odorant or aromatic substance is brought into contact with or mixed with a product.
4. Verfahren zum Modifizieren und/oder Verstärken (Boosten) eines Geruchs und/oder Geschmacks mit einer, mehreren oder sämtlichen der Noten frisch, fruchtig und/oder süß, mit folgendem Schritt: 4. A method for modifying and / or enhancing (boosting) an odor and / or taste with one, several or all of the notes fresh, fruity and / or sweet, with the following step:
- Vermischen eines oder mehrerer Riech- oder Aromastoffe mit einer, mehreren oder sämtlichen der Noten frisch, fruchtig und/oder süß, mit einer Menge an 2-Methoxymethylphenol, die ausreicht, den Geruchs- und/oder Geschmackseindruck des bzw. der Riech- oder Aromastoffe, die eine oder mehrere der Noten frisch, fruchtig und/oder süß verursachen, sensorisch zu modifizieren und/oder zu verstärken. - Mixing one or more fragrance or aroma substances with one, several or all of the notes fresh, fruity and / or sweet, with an amount of 2-methoxymethylphenol which is sufficient to give the odor and / or taste impression of the odorant or Aroma substances that cause one or more of the notes fresh, fruity and / or sweet to be modified by sensors and / or intensified.
5. Riech- oder Aromastoffkomposition, umfassend 5. Fragrance or flavor composition, comprising
2-Methoxymethylphenol und  2-methoxymethylphenol and
einen oder mehrere weitere Riech- oder Aromastoffe,  one or more other odoriferous or aromatic substances,
wobei (i) die Menge an 2-Methoxymethylphenol ausreicht, eine, mehrere oder sämtliche der Noten vanillig, nelkig und/oder ledrig zu vermitteln und/oder (ii) der oder die weiteren Riech- oder Aromastoffe eine, mehrere oder sämtliche der Noten vanillig, nelkig, ledrig frisch, fruchtig und/oder süß vermitteln und die Menge an 2-Methoxymethylphenol ausreicht, eine oder mehrere dieser Noten zu Modifizieren und/oder zu Verstärken (zu Boosten) und/oder (iii) die Menge an 2-Methoxymethylphenol ausreicht, der Riech- oder Aromastoffkomposition (Aus)Strahlung, Glanz, Abrundung, Natürlichkeit und/oder Harmonie zu verleihen. where (i) the amount of 2-methoxymethylphenol is sufficient to impart one, several or all of the notes vanilla, carnation and / or leathery and / or (ii) the other fragrance or aroma substances convey one, several or all of the notes vanilla, clove-like, leathery fresh, fruity and / or sweet and the amount of 2-methoxymethylphenol is sufficient to modify one or more of these notes and / or to reinforce (to boost) and / or (iii) the amount of 2-methoxymethylphenol is sufficient to give the fragrance or flavoring composition (out) radiation, gloss, roundness, naturalness and / or harmony.
6. Riech- oder Aromastoffkomposition nach Anspruch 5, wobei der oder die weiteren Riech- oder Aromastoffe ausgewählt sind aus der Gruppe bestehend aus: 6. fragrance or aroma substance composition according to claim 5, wherein the further fragrance or aroma substances are selected from the group consisting of:
2-Methyl-buttersäureethylester, 4-(p-Hydroxyphenyl)-2-butanon, Ethyl-3-methyl- 3-phenylglycidat, Buttersäureisoamylester, Essigsäureisoamylester, Essigsäure- n-butylester, Buttersäureethylester, 3-Methyl-buttersäureethylester, n- Hexansäureethylester, n-Hexansäureallylester, Ethyl-2-trans-4-cis-decadienoat, 1 ,1 -Dimethoxy-2,2,5-trimethyl-4-hexan, 2,6-Dimethyl-5-hepten-1-al, gamma- Undecalacton, gamma-Nonalacton, Vanillin, Ethylvanillin, Maltol, Ethylmaltol und deren Mischungen. 2-methyl-butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl 3-methyl-3-phenylglycidate, butyric acid isamyl ester, acetic acid isoamyl ester, acetic acid n-butyl ester, butyric acid ethyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid allyl ester, ethyl 2-trans-4-cis decadienoate, 1, 1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, gamma Undecalactone, gamma-nonalactone, vanillin, ethylvanillin, maltol, ethylmaltol and mixtures thereof.
7. Riech- oder Aromastoffkomposition nach Anspruch 5 oder 6, wobei die Riech- oder Aromastoffkomposition eine Menge an 2-Methoxymethylphenol im Bereich von 0,0001 bis 90 Gew.-%, vorzugsweise 0,01 bis 70 Gew.-% und besonders bevorzugt 0,1 bis 50 Gew.-%, umfasst, bezogen auf die Gesamtmenge der Riech- oder Aromastoffkomposition. 7. fragrance or flavoring composition according to claim 5 or 6, wherein the fragrance or flavoring composition an amount of 2-methoxymethylphenol in the range of 0.0001 to 90 wt .-%, preferably 0.01 to 70 wt .-% and particularly preferred 0.1 to 50 wt .-%, based on the total amount of the fragrance or flavoring composition.
8. Riech- oder Aromastoffkomposition nach Anspruch 5 oder 6, wobei die Riech- oder Aromastoffkomposition eine Menge an 2-Methoxymethylphenol im Bereich von 0,01 bis 5 Gew.-%, vorzugsweise 0,1 bis 2 Gew.-%, umfasst, bezogen auf die Gesamtmenge der Riech- oder Aromastoffkomposition. 8. fragrance or flavoring composition according to claim 5 or 6, wherein the fragrance or flavoring composition comprises an amount of 2-methoxymethylphenol in the range from 0.01 to 5% by weight, preferably 0.1 to 2% by weight, based on the total amount of the fragrance or flavoring composition.
9. Verfahren zur Herstellung einer Riech- oder Aromastoffkomposition, mit folgendem Schritt: Vermischen von 2-Methoxymethylphenol mit üblichen Bestandteilen einer9. A method for producing a fragrance or flavoring composition, comprising the following step: Mixing 2-methoxymethylphenol with common ingredients
Riech- oder Aromastoffkomposition, wobei das 2-Methoxymethylphenol in einerFragrance or flavoring composition, the 2-methoxymethylphenol in one
Menge eingesetzt wird, die ausreicht, um in der Riech- oder Aromastoffkomposi- tion eine Geruchs- oder Geschmacksnote zu vermitteln, zu modifizieren und/oder zu verstärken. Amount is used that is sufficient to impart, modify and / or enhance an odor or taste note in the fragrance or flavoring composition.
10. Verfahren nach Anspruch 9 zur Herstellung einer Riech- oder Aromastoffkomposition mit fruchtiger, frischer und/oder süßer Note, wobei die üblichen Bestandteile der Riech- oder Aromastoffkomposition Riech- oder Aromastoffe umfassen, die ausgewählt sind aus der Gruppe bestehend aus: 2-Methyl-buttersäureethylester, 4-(p-Hydroxyphenyl)-2-butanon, Ethyl-3-methyl- 3-phenylglycidat, Buttersäureisoamylester, Essigsäureisoamylester, Essigsäure- n-butylester, Buttersäureethylester, 3-Methyl-buttersäureethylester, n- Hexansäureethylester, n-Hexansäureallylester, Ethyl-2-trans-4-cis-decadienoat, 1 ,1 -Dimethoxy-2,2,5-trimethyl-4-hexan, 2,6-Dimethyl-5-hepten-1-al, gamma- Undecalacton, gamma-Nonalacton, Vanillin, Ethylvanillin, Maltol, Ethylmaltol und deren Mischungen. 10. The method according to claim 9 for the production of a fragrance or flavoring composition with a fruity, fresh and / or sweet note, the usual constituents of the fragrance or flavoring composition comprising fragrance or flavoring substances selected from the group consisting of: 2-methyl -butyric acid ethyl ester, 4- (p-hydroxyphenyl) -2-butanone, ethyl 3-methyl-3-phenylglycidate, butyric acid isoamyl ester, acetic acid isoamyl ester, acetic acid - n-butyl ester, butyric acid ethyl ester, 3-methyl-butyric acid ethyl ester, n-hexanoic acid ethyl ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoic acid ester, n-hexanoate ester , Ethyl 2-trans-4-cis decadienoate, 1,1-dimethoxy-2,2,5-trimethyl-4-hexane, 2,6-dimethyl-5-hepten-1-al, gamma-undecalactone, gamma -Nonalactone, vanillin, ethylvanillin, maltol, ethylmaltol and mixtures thereof.
1 1. Verwendung von 2-Methoxymethylphenol oder einer 2- Methoxymethylphenol enthaltenden Mischung als Mittel zum Versehen von (a) Haaren oder (b) textilen Fasern mit einem vanilligen, nelkigen und/oder ledrigen Duft. 1 1. Use of 2-methoxymethylphenol or a mixture containing 2-methoxymethylphenol as a means of providing (a) hair or (b) textile fibers with a vanilla, carnation and / or leathery fragrance.
12. Verwendung von 2-Methoxymethylphenol als Mittel zum Erhöhen der Sub- stantivität und/oder Retention einer Riechstoffmischung und/oder als Fixateur. 12. Use of 2-methoxymethylphenol as an agent for increasing the substance and / or retention of a fragrance mixture and / or as a fixator.
13. Verfahren zum Versehen von (a) Haaren oder (b) textilen Fasern mit einem vanilligen, nelkigen und/oder ledrigen Duft, mit folgenden Schritten: - Bereitstellen einer 2-Methoxymethylphenol enthaltenden Mischung, Applizieren der Mischung auf das Haar oder die textilen Fasern. 13. A method for providing (a) hair or (b) textile fibers with a vanilla, carnation and / or leathery fragrance, with the following steps: - providing a mixture containing 2-methoxymethylphenol, applying the mixture to the hair or the textile fibers .
14. Verfahren zum Versehen von (a) Haaren oder (b) textilen Fasern mit einem fruchtigen, frischen und/oder süßen Geruch, mit folgenden Schritten: Bereitstellen einer Riechstoffmischung umfassend 2-Methoxymethylphenol und einen oder mehrere weitere Riechstoffe, der bzw. die eine, mehrere oder sämtliche der Noten frisch, fruchtig und/oder süß vermitteln, wobei die Menge an14. A method for providing (a) hair or (b) textile fibers with a fruity, fresh and / or sweet smell, with the following steps: Provision of a fragrance mixture comprising 2-methoxymethylphenol and one or more further fragrances which convey one, several or all of the notes fresh, fruity and / or sweet, the amount of
2-Methoxymethylphenol ausreicht, eine oder mehrere dieser Noten zu modifizie- ren und/oder zu verstärken (zu boosten), 2-methoxymethylphenol is sufficient to modify and / or enhance (to boost) one or more of these notes,
Applizieren der Mischung auf das Haar oder die textilen Fasern. Apply the mixture to the hair or textile fibers.
15. Lösung umfassend Wasser 2-Methoxymethylphenol sowie - ein oder mehrere Tenside, wobei die Konzentration an 2-Methoxymethylphenol in der Lösung im Bereich von 10"7-10"1 Gew.-% liegt. 15. Solution comprising water 2-methoxymethylphenol and - one or more surfactants, the concentration of 2-methoxymethylphenol in the solution being in the range from 10 "7 -10 " 1 % by weight.
16. Verwendung nach Anspruch 1 1 oder Verfahren nach Anspruch 13 oder 14, wobei die 2-Methoxymethylphenol enthaltende Mischung eine Lösung nach Anspruch 15 ist. 16. Use according to claim 1 1 or method according to claim 13 or 14, wherein the mixture containing 2-methoxymethylphenol is a solution according to claim 15.
17. Verwendung von 2-Methoxymethylphenol als Mittel zum Erhöhen des über einer tensidhaltigen wässrigen Lösung wahrgenommenen Geruches anderer Riechstoffe. 17. Use of 2-methoxymethylphenol as a means of increasing the smell of other fragrances perceived over a surfactant-containing aqueous solution.
18. Mischung umfassend 2-Methoxymethylphenol und ein oder mehrere Tensi- de, die ausgewählt sind aus der Gruppe bestehend aus: Lineare Alkylbenzolsul- fonate, Fettalkoholethoxylate mit 12-18 C-Atomen, Laurylethersulfate und Betaine. 18. Mixture comprising 2-methoxymethylphenol and one or more surfactants which are selected from the group consisting of: linear alkylbenzenesulfonates, fatty alcohol ethoxylates with 12-18 C atoms, lauryl ether sulfates and betaines.
19. Produkt umfassend eine Riech- oder Aromastoffkomposition nach einem der Ansprüche 5-8. 19. Product comprising a fragrance or flavoring composition according to any one of claims 5-8.
PCT/EP2006/067646 2005-12-09 2006-10-23 2-methoxymethylphenol as perfume and aroma substance WO2007065755A1 (en)

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