EP1878787B1 - Aldehydes substituted with alkyls in alpha position as odorous and aroma substances - Google Patents

Description

The present invention relates to the use of certain alpha-substituted by an alkyl radical aldehydes having a total of 13 or a total of 15 carbon atoms as fragrances or flavorings. The invention also relates to perfumed or flavored articles comprising such aldehydes and corresponding processes for imparting, modifying and / or enhancing certain odor and / or flavor notes.

Also described are methods for preparing suitable aldehydes and aldehyde mixtures.

Despite a large number of already existing fragrances, there is still a general need in the perfume industry for new fragrances. Thus, there is a need for fragrances with aldehydigen fragrance notes, which are able to produce (in fragrance compositions) in addition to an aldehydigen fragrance note more interesting odor notes and to extend the possibilities of the perfumer with their novel or original fragrance properties. In particular, there is an interest in fragrances with aldehydic scents which are capable are to make a harmonious combination with woody scented fragrances. Preferably, a superimposition of the different odoriferous aspects and notes should take place in order thereby to produce an overall complex olfactory impression.

For the creation of novel modern compositions there is a constant need for fragrances with special odor properties, which are suitable to serve as a basis for the composition of novel modern perfumes with complex odor character. Preferred odoriferous substances sought should have, in addition to an aldehydic fragrance, further notes and aspects that give them an odor character and complexity.

• Die Mechanismen der Geruchswahrnehmung sind nicht ausreichend bekannt.
• Die Zusammenhänge zwischen der speziellen Geruchswahrnehmung einerseits und der chemischen Struktur des zugehörigen Riechstoffs andererseits sind nicht hinreichend erforscht.
• Häufig bewirken bereits geringfügige Änderungen am strukturellen Aufbau eines bekannten Riechstoffs starke Änderungen der sensorischen Eigenschaften und beeinträchtigen die Verträglichkeit für den menschlichen Organismus.

The search for suitable fragrances which led to the present invention was hampered by the following facts:

• The mechanisms of smell perception are not sufficiently known.
• The connections between the special smell perception on the one hand and the chemical structure of the corresponding fragrance on the other hand, have not been sufficiently researched.
• Often, even minor changes in the structural makeup of a known fragrance cause significant changes in sensory properties and affect tolerability to the human organism.

The success of finding suitable fragrances therefore depends heavily on the intuition of the searcher.

Therefore, the object underlying this invention was essentially to find fragrances with aldehydigen fragrances, which are paired with other interesting and original odor properties, whereby the fragrances sought novel and original fragrance compositions with enable particular odor notes and aspects. In particular, fragrances with aldehydigen fragrances should be found, which are particularly suitable for combination with fragrances, which have a woody fragrance.

In addition, the perfumes that accomplish this main purpose should also preferably have additional positive secondary properties beyond their primary, namely, odoriferous, properties, such as, e.g. a higher stability under certain conditions of use, a higher yield, a better adhesion, a high substantivity, a remarkable booster effect or a strong blooming, so that sensory remarkable effects or else better dermatological and toxicological properties can be achieved compared to similar fragrances.

mit

1. (I) insgesamt 13 C-Atomen, wobei
   R einen unverzweigten Alkylrest mit 6, 7, 8 oder 9 C-Atomen und
   R' einen unverzweigten Alkylrest mit 2, 3, 4 oder 5 C-Atomen bedeutet,
   oder
2. (II) insgesamt 15 C-Atomen, wobei
   R einen unverzweigten Alkylrest mit 8, 9, 10 oder 11 C-Atomen und
   R' einen unverzweigten Alkylrest mit 2, 3, 4 oder 5 C-Atomen bedeutet,
   oder einer Mischung umfassend oder bestehend aus zwei, drei oder mehr solcher Aldehyde des Typs (I) und/oder (II),
   als Riech- oder Aromastoff.

According to the invention, the primary object is achieved by the use of an alpha-substituted by an alkyl radical aldehyde of the formula

With

1. (I) a total of 13 carbon atoms, wherein
   R is an unbranched alkyl radical having 6, 7, 8 or 9 C atoms and
   R 'is an unbranched alkyl radical having 2, 3, 4 or 5 C atoms,
   or
2. (II) a total of 15 carbon atoms, where
   R is an unbranched alkyl radical having 8, 9, 10 or 11 C atoms and
   R 'is an unbranched alkyl radical having 2, 3, 4 or 5 C atoms,
   or a mixture comprising or consisting of two, three or more such aldehydes of the type (I) and / or (II),
   as a scent or flavoring.

mit

1. (I) insgesamt 13 C-Atomen, wobei
   R einen unverzweigten Alkylrest mit 6, 7, 8 oder 9 C-Atomen und
   R' einen unverzweigten Alkylrest mit 2, 3, 4 oder 5 C-Atomen bedeutet,
   oder
2. (II) insgesamt 15 C-Atomen, wobei
   R einen unverzweigten Alkylrest mit 8, 9, 10, 11 oder 12 C-Atomen und
   R' einen unverzweigten Alkylrest mit 1, 2, 3, 4 oder 5 C-Atomen bedeutet,

oder einer Mischung umfassend oder bestehend aus zwei, drei oder mehr solcher Aldehyde des Typs (I) und/oder (II),
als Riech- oder Aromastoff mit coniferiger Note.The stated object is also achieved by the use of an alpha-substituted by an alkyl radical aldehyde of the formula

With

1. (I) a total of 13 carbon atoms, wherein
   R is an unbranched alkyl radical having 6, 7, 8 or 9 C atoms and
   R 'is an unbranched alkyl radical having 2, 3, 4 or 5 C atoms,
   or
2. (II) a total of 15 carbon atoms, where
   R is an unbranched alkyl radical having 8, 9, 10, 11 or 12 C atoms and
   R 'is an unbranched alkyl radical having 1, 2, 3, 4 or 5 C atoms,

or a mixture comprising or consisting of two, three or more such aldehydes of the type (I) and / or (II),
as a scent or flavoring with a coniferous note.

Further aspects emerge from the attached patent claims and the following description; In particular, these aspects concern new perfumed or flavored articles and related procedures.

und besitzen zwei unverzweigte Alkylreste R bzw. R'. Die erfindungsgemäß zu verwendenden Aldehyde, die jeweilige Gesamtanzahl von C-Atomen sowie die jeweilige Anzahl von C-Atomen in den Resten R und R' ergibt sich aus der nachfolgenden Tabellle. Tabelle 1: Übersicht über die erfindungsgemäß zu verwendenden Aldehyde Erfindungsgemäß zu verwendende Aldehyde Anzahl C-Atome insgesamt Anzahl C-Atome in R Anzahl C-Atome in R' 2-Ethyl-undecanal 13 9 2 2-Propyl-decanal 13 8 3 2-Butyl-nonanal 13 7 4 2-Pentyl-octanal 13 6 5 2-Methyltetradecanal 15 12 1 2-Ethyl-tridecanal 15 11 2 2-Propyldodecanal 15 10 3 2-Butyl-undecanal 15 9 4 2-Pentyl-decanal 15 8 5 The aldehydes to be used according to the invention are aldehydes having a total of 13 or a total of 15 C atoms. The aldehydes to be used are those of the formula

and have two unbranched alkyl radicals R and R '. The aldehydes to be used according to the invention, the respective total number of C atoms and the respective number of C atoms in the radicals R and R 'are shown in the table below. Table 1: Overview of the aldehydes to be used according to the invention Aldehydes to be used according to the invention Total C-atoms in total Number of C atoms in R Number of C atoms in R ' 2-ethyl-undecanal 13 9 2 2-propyl-decanal 13 8th 3 2-butyl-nonanal 13 7 4 2-pentyl-octanal 13 6 5 2-methyltetradecanal 15 12 1 2-ethyl-tridecanal 15 11 2 2-Propyldodecanal 15 10 3 2-butyl-undecanal 15 9 4 2-Pentyl-decanal 15 8th 5

The odor properties of the aldehydes to be used according to the invention (see Table 1) are each described as follows: strongly aldehydic, clearer than other aldehydes, strongly coniferous, flowery, greasy sweet, ozone. In particular, the aldehydes of type (I) or (II) can be used for imparting, modifying and / or enhancing a corresponding odor and / or flavor.

The suitability of the aldehydes listed in Table 1, d. H. the aldehydes to be used according to the invention, as fragrances or flavorings for use in the olfactory and flavor industry, have not hitherto been known and are surprising.

in the Journal of Organic Chemistry (1978), 43 (14) 2907-2910 Among other things, the preparation of 2-butyl-nonanal is described. However, a sensory description of this compound has not been given.

The German patent DE 43 44 064 C1 discloses processes for the preparation of alpha-alkyl substituted aldehydes. One example relates to the preparation of isomeric tridecanals from 1-dodecene. A sensory description of the produced aldehydes can be found in the DE 43 44 064 C1 Not. Instead, it is stated that aldehydes containing 8 to 17 carbon atoms, which are substituted by alkyl radicals in the alpha position to the carbonyl group, have technical significance as intermediates.

The German patent application DE 39 42 954 A1 describes processes for the preparation of aldehydes by hydroformylation of olefinically unsaturated compounds. The DE 39 42 954 A1 contains no sensory descriptions of the aldehydes produced.

In the Journal Fette, Soaps, Anstrichmittel (1974), 76 (10), 443-446 Among other things, there are indications for the synthesis of branched aldehydes by hydroformylation of isomerized alkenes. A sensory description of the branched aldehydes prepared is not found in the publication.

US 2006/0003913 discloses liquid detergent formulations containing fragrance aldehydes such as undecyl aldehyde, dodecyl aldehyde or 2-methyl undecanal.

US 4,304,689 describes branched-chain C ₁₁ aliphatic aldehydes and mixtures thereof, their use and odor-raising activity in perfume oils and perfumed articles.

From S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, self-publisher, the aldehydes tridecanal, methyldecylacetaldehyde (2-methyl-dodecanal) and pentadecanal are already known. There are also odor descriptions, which can be summarized as follows: tridecanal: strongly waxy-greasy, freshly citrusy, slightly flowery. Methyldecylacetaldehyd: dry waxy. pentadecanal: very weak, fresh-flowery.

The aldehydes pentadecanal, methyldecylacetaldehyde and tridecanal are in the said publication (S. Arctander) as a whole for the perfumery not very interesting classified. Most interesting for perfumery, according to the published data, is the tridecanal, which, however, is an unbranched aldehyde and whose odor properties differ significantly from those of the aldehydes to be used according to the invention (see Table 1 above).

See CAS Registry Number 93821-14-8 for specific hydroformylation products of C12-14 alkenes. A reference to a corresponding product can be found on the Internet in a publication by Celanese Chemicals. This is followed by the CAS number 93821-14-8, a mixture of n / i tridecanal and n / i pentadecanal. However, an odor description of the individual aldehydes contained in the mixture is not found. In particular, there is no odor description for i-pentadecanal, d. H. the compound according to the invention to be used 2-methyl-tetradecanal. In particular, there is no indication that this compound has a strong coniferigen odor.

Other already known aldehydes have, according to statements in the literature, a sweet, greasy-waxy, fresh-flowery odor with a slightly balsamic undertone (lauric aldehyde) or strongly diffuse herbaceous aldehydic odor notes with a dry amber undertone (methyl undecanal).

The present invention is based inter alia on the surprising finding in the light of the prior art that the aldehydes to be used according to the invention (see Table 1 above) have similar and moreover better or different odor properties than those already present with regard to their odor properties aldehydes tridecanal, methyldecylacetaldehyde and pentadecanal described. Surprisingly, therefore, the aldehydes to be used according to the invention are particularly suitable as fragrances and flavorings.

In view of the above-described odor properties of the aldehydes to be used according to the invention, these are used in particular for imparting, modifying and / or enhancing an odor and / or flavor with the following aspects: aldehydic, coniferous, flowery, greasy sweet, ozone.

The aldehydes to be used according to the invention are usually used in sensory effective amounts in the context of the use according to the invention. Frequently, the aldehydes to be used according to the invention are to be mixed with other fragrances or flavorings. These other fragrances or flavorings may be other aldehydes (including the above-mentioned aldehydes tridecanal, methyldecylacetaldehyde and pentadecanal) or other fragrances or flavorings. The weight ratio of the total amount of fragrances to be used according to the invention (i.e., the fragrances listed in Table 1) to the total amount of other fragrances or flavorings is preferably in the range of 1: 1000 to 1: 0.5.

Particularly preferred is the use of a mixture comprising or consisting of two, three or more aldehydes of the type (I) and / or the type (II). As is apparent from the information below on preferred manufacturing method for aldehydes to be used according to the invention with a total of 13 or 15 carbon atoms, it is particularly easy to produce such aldehyde mixtures, and using the preferred manufacturing process, it would require additional effort to isolate individual prepared aldehydes having a total of 13 or 15 carbon atoms and to use isolated from other aldehydes present in the prepared aldehyde mixture.

The combination of aldehydes to be used according to the invention with woody fragrances (including sandal, musk and amber) and floral fragrances is particularly suitable. Sandryol (2-ethyl-4- (2,2,3) -trimethylcyclopent-3-yl-but-2-en-1-ol), Ysamber K (1 ', 1', 5 ', 5'-tetramethylhexahydro-spiro [1,3-dioxolane-2,8'(5'H) -2H-2,4a-methanonaphthalene]), globanone (cyclohexadec-8-en-1-one), timberol (1- (2,2,6-trimethylcyclohexyl) hexan-3-ol), Iso-E-Super (2,3,8,8, -tetramethyl-1,2,3,4,5,6,8- octahydro-2-naphthalenyl methyl ketone) Cashmeran (1,1,2,3,3-pentamethyl TH-indan-4-one), isobornyl acetate (2-exo-bornanyl acetate), ylanate (2-tert-butylcyclohexyl acetate). Especially suitable for combination flowery fragrances are: Lilial (2-methyl-3- (4-tert-butylphenyl) propanal), hedione (methyl (3-oxo-2-pentylcyclopentyl) acetate), Mayol (4-isopropyl-cyclohexyl) methanol ), Linalool (3,7-dimethyl-1,6-octadien-3-ol), dihydromyrcenol (2,6-dimethyl-7-octene-2-ol), citronellol (3,7-dimethyl-6-octene) 1-ol), phenoxanol (3-methyl-5-phenylpentanol), 2-phenylethyl alcohol, hydroxycitronellal (3,7-dimethyl-7-hydroxyoctan-1-al), alpha-ionone (4- (2,6, 6-trimethyl-cyclohex-2-enyl) -but-3-en-2-one).

The combination of aldehydes to be used according to the invention with the aforementioned woody fragrances leads to brighter and cleaner odor impressions. The mixtures are more natural and fresher.

The effect when combined with floral fragrances goes in the direction of freshness and charisma. Furthermore, the flowery aspects are reinforced. The mixtures smell more intense and harmonious.

Furthermore, a combination with green-fruity fragrances is often particularly preferred. Suitable green-fruity fragrances are, for example: Vertral (octahydro-1 H-4,7-methanoindene-5-carbaldehyde), cis-3-hexene-1-ol, beta-damascone (1- (2,6,6-trimethyl -cyclohex-2-enyl) -butene-1-one), vertocitral (2,4-dimethylcyclohex-3-en-1-carbaldehyde), cyclogalbanate (allyl (cyclohexyloxy) acetate), hexyl acetate.

The combination with above-mentioned fragrances results in a rounder and softer smell. In addition, an impression of florality and a natural appearance is mediated by the addition of the aldehydes of the invention.

Furthermore, a combination with spicy-balsamic fragrances is often preferred. Suitable spicy-balsamic fragrances are in particular: eugenol (2-methoxy-4-allylphenol), coumarin (2H-1-benzopyran-2-one), anisaldehyde (4-methoxybenzaldehyde), amyl cinnamaldehyde (2-pentyl-3-phenyl-2 -propenal), isoamylsalicylate (Salicylic acid 3-methylbutyl ester) and cinnamyl alcohol (3-phenyl-2-propen-1-ol).

In the combination of inventive aldehydes with the fragrances mentioned aspects of freshness and naturalness are observed. The mixtures are more harmonious and radiant.

The compounds according to the invention to be used according to Table 1 each have a chiral center; they may be R- or S-configured or used as any mixture of the enantiomers, in particular as a racemate.

It is particularly surprising that the compounds according to the invention to be used according to Table 1 (aldehydes of type (I) and (II)) have an expressive aldehydic odor, each with additional, sometimes very complex and multi-faceted aspects, because of the presence of these additional additional aspects The compounds to be used according to the invention differ very markedly from structurally comparable and known substances with aldehydic odor notes. Compare in particular the above information on tridecanal, methyldecylacetaldehyde and pentadecanal. In addition to their primary aldehydic scent note, the aldehydes or aldehyde mixtures to be used according to the invention have, in particular, an unexpectedly strong coniferous and sweet odor with a surprising range of complex olfactory shades. In particular, the mixtures of aldehydes to be used according to the invention and in particular mixtures of aldehydes of the formulas (I) and (II), d. H. of aldehydes having 13 and 15 carbon atoms to be used according to the invention give a very complex and varied odor and taste impression which otherwise can only be achieved by complex mixtures of several components (such as, for example, essential oils or herbal or spice mixtures).

The use of mixtures of aldehydes to be used according to the invention is preferred, the mixtures comprising one, two or more aldehydes of type (I) and one, two or more aldehydes of type (II) and the Weight ratio of the total amount of aldehydes of type (I) to the total amount of aldehydes of type (II) in the range of 100: 1 to 1:10, preferably in the range of 10: 1 to 1: 2, and more preferably in the range of 8 : 1 to 1: 1. Very particularly preferred is a mixing ratio in the range of 5: 1 to 2: 1.

If the aldehydes to be used according to the invention are to be combined with pentadecanal, methyldecylacetaldehyde and / or tridecanal, the weight ratio of the total amount of aldehydes of the type (I) and (II) to the total amount of pentadecanal, methyldecylacetaldehyde and tridecanal is preferably in the range from 1: 1000 to 1 : 0.1.

In mixtures with other fragrances, the compounds of the formulas (I) and (II) to be used according to the invention are able to intensify the intensity of a fragrance mixture even at low dosages and to round off and harmonize the overall appearance of the fragrance mixture and to add more (off) radiation and naturalness to the mixture to lend.

In the context of the inventive use of the abovementioned aldehydes of the type (I) and (II) as a fragrance or flavoring substance (in particular with a coniferous note), the present invention also relates to the use for providing (a) hair, (b) skin or ( c) textile fibers with a - in particular aldehydigen and at the same time coniferigen - scent (with regard to further smell or taste notes see above). The present invention also relates to corresponding processes and (preferably surfactant-containing) mixtures. According to a related aspect, the present invention also relates to the use of the above-mentioned aldehydes of the type (I) or (II) or a mixture comprising or consisting of two, three or more such aldehydes of the type (I) and / or (II) as Means for increasing the substantivity and / or retention of a fragrance mixture and / or as a fixative and / or as an agent for increasing the perceived via a surfactant-containing aqueous solution odor of other fragrances.

In connection with the preferred use for modifying and / or enhancing an odor and / or flavor, there is also the recognition that the aldehydes of type (I) and / or (II) or the corresponding mixtures to be used according to the invention are outstandingly known as boosters (Amplifier) can act.

The aldehydes of the type (I) or (II) or the corresponding mixtures to be used according to the invention have, in addition to their primary, namely olfactory properties, additional positive secondary properties, such as, for example, B. a high stability under certain conditions of use, high yield, good adhesion, high substantivity.

Aldehydes of type (I) and / or (II) or corresponding mixtures can be used, in particular, to impart radiation, rounding off and / or harmony to a fragrance or aroma composition (off) and / or to existing odor and / or taste notes strengthen.

1. (a) einen in alpha-Stellung durch einen Alkylrest substituierten Aldehyd der Formel
   
   mit
   1. (I) insgesamt 13 C-Atomen, wobei
      R einen unverzweigten Alkylrest mit 6, 7, 8 oder 9 C-Atomen und
      R' einen unverzweigten Alkylrest mit 2, 3, 4 oder 5 C-Atomen bedeutet,
      oder
   2. (II) insgesamt 15 C-Atomen, wobei
      R einen unverzweigten Alkylrest mit 8, 9, 10, 11 oder 12 C-Atomen und
      R' einen unverzweigten Alkylrest mit 1, 2, 3, 4 oder 5 C-Atomen bedeutet,
   oder eine Mischung umfassend oder bestehend aus zwei, drei oder mehr solcher Aldehyde des Typs (I) und/oder (II),
   vorzugsweise in einer Menge, die ausreicht, eine Geruchs- oder Geschmacksnote des Typs aldehydisch, coniferig, blumig, fettig süß und/oder ozonig zu vermitteln, zu modifizieren und/oder zu verstärken sowie
2. (b) einen, zwei, drei oder mehr weitere Riech- oder Aromastoffe, bei denen es sich jeweils nicht um einen Aldehyd mit 13 oder 15 C-Atomen handelt, wobei der oder die weiteren Riech- oder Aromastoffe vorzugsweise einen holzigen und/oder blumigen Geruch und/oder Geschmack vermitteln.
   Hinsichtlich der Kombination mit besonders bevorzugten Riech- oder Aromastoffen mit holziger und/oder blumiger Geruchsnote sei auf die Ausführungen weiter oben verwiesen.
   Die vorstehend mit Blick auf die erfindungsgemäßen Verwendungen beschriebenen bevorzugten Ausgestaltungen der Erfindung gelten entsprechend auch für erfindungsgemäße parfümierte aromatisierte Artikel, insbesondere die Angaben zu bevorzugten Gewichtsverhältnissen.
   Vorzugsweise umfasst ein erfindungsgemäßer parfümierter oder aromatisierter Artikel neben den Komponenten (a) und (b) auch
3. c) ein, zwei oder sämtliche Aldehyde aus der Gruppe bestehend aus Pentadecanal, Methyldecylacetaldehyd (2-Methyl-dodecanal) und Tridecanal.
   Die Kombination der Komponente (a) mit der Komponente (c) ist insbesondere deshalb bevorzugt, weil es bei geeigneter Verfahrensführung möglich ist, Aldehyde der Komponenten (a) und (c) in einem gemeinsamen Reaktionsansatz herzustellen. Abhängig von der konkreten Verfahrensgestaltung ist es dabei möglich, die Anteile der besagten Aldehyde zu variieren. Zu Herstellungsverfahren, welche zu Mischungen der Komponenten (a) und (c) führen, s. weiter unten.

The present invention also relates to perfumed or flavored articles comprising

1. (A) an alpha-substituted by an alkyl radical aldehyde of the formula
   
   With
   1. (I) a total of 13 carbon atoms, wherein
      R is an unbranched alkyl radical having 6, 7, 8 or 9 C atoms and
      R 'is an unbranched alkyl radical having 2, 3, 4 or 5 C atoms,
      or
   2. (II) a total of 15 carbon atoms, where
      R is an unbranched alkyl radical having 8, 9, 10, 11 or 12 C atoms and
      R 'is an unbranched alkyl radical having 1, 2, 3, 4 or 5 C atoms,
   or a mixture comprising or consisting of two, three or more such aldehydes of the type (I) and / or (II),
   preferably in an amount sufficient to impart, modify and / or enhance an odor or flavor note of the type aldehydic, coniferous, flowery, greasy sweet and / or ozone, and
2. (b) one, two, three or more other fragrances or flavorings, each of which is not an aldehyde of 13 or 15 carbon atoms, said or each other fragrance or flavoring preferably being a woody and / or floral Convey smell and / or taste.
   With regard to the combination with particularly preferred fragrances or flavorings with a woody and / or floral odor note, reference is made to the comments above.
   The preferred embodiments of the invention described above with a view to the uses according to the invention also apply correspondingly to perfumed flavored articles according to the invention, in particular the details of preferred weight ratios.
   Preferably, a perfumed or flavored article according to the invention also comprises, in addition to components (a) and (b)
3. c) one, two or all aldehydes selected from the group consisting of pentadecanal, methyldecylacetaldehyde (2-methyl-dodecanal) and tridecanal.
   The combination of component (a) with component (c) is particularly preferred because it is possible with suitable process control, aldehydes of components (a) and (c) in a common reaction mixture manufacture. Depending on the specific process design, it is possible to vary the proportions of said aldehydes. For manufacturing processes which lead to mixtures of components (a) and (c), s. further down.

Preferably, a perfumed or flavored article of the invention is a fragrance or flavoring composition. By combining the component (a) with a component (b), ie with one, two, three or more other fragrances or flavorings (preferably having a woody and / or floral odor or taste), new fragrance or flavoring compositions can be formed. In this way you can create particularly interesting and natural new and original fragrances. Fragrances (as component (b)), which are advantageously suitable for combination, are found, for. In S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, self-published , or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001 , Specifically, may be mentioned:

Extracts from natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balms, tinctures such. B.

ambergris tincture; Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil; Basil oil; Tree Moss -Absolue; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; birch tar; Bitter almond oil; Savory oil; Buccoblätteröl; Cabreuvaöl; cade oil; calamus; camphor oil; Cananga oil; cardamom; Cascarillaöl; cassia; Cassie absolute; Beaver-absolue; Cedernblätteröl; cedarwood; cistus; citronella; lemon; copaiba balsam; Copaivabalsamöl; Coriander oil; costus root; Cuminöl; Cypress oil; Davanaöl; Dill herb oil; Dill seed oil; Eau de Brouts absolute; Oak moss absolute; elemi; Tarragon oil; Eucalyptus citriodora oil; eucalyptus oil; Fennel oil; Pine needle oil; galbanum; Galbanumresin; geranium; Grapefruit oil; guaiac wood; gurjun balsam; gurjun balsam oil; Helichrysum absolute; Helichrysumöl; Ginger oil; Iris root absolute; Orris root oil; Jasmine absolute; calamus; Chamomile oil blue; Camomile oil Roman; Carrot seed oil; Kaskarillaöl; Pine needle oil; spearmint; Seed oil; labdanum; Labdanum absolute; Labdanumresin; Lavandin absolute; Lavandin oil; Lavender absolute; Lavender oil; Lemongrass oil; Lovage oil; Distilled lime oil; Pressed lime oil; linaloe; Litsea cubeba oil; Bay leaf oil; Macisöl; Marjoram oil; Mandarin oil; Massoirindenöl; Mimosa absolute; Musk seed oil; musk tincture; Clary sage oil; nutmeg; Myrrh absolute; Myrrh oil; myrtle; Clove leaf oil; Clove flower oil; neroli; Olibanum absolute; olibanum; Opopanaxöl; Orange blossom absolute; Orange oil; oregano; Palmarosa oil; patchouli oil; perilla oil; Peruvian balsam oil; Parsley leaf oil; Parsley seed oil; Petitgrain oil; Peppermint oil; Pepper oil; chilli; pine oil; Poleyöl; Rose absolute; Rosewood oil; Rose oil; Rosemary oil; Sage oil Dalmatian; Sage oil spanish; sandalwood; Celery seed oil; spike lavender oil; star anise; Styraxöl; tagetes; Pine needle oil; Tea-tree oil; turpentine; Thyme oil; Tolu; Tonka absolute; Tuberose absolute; Vanilla extract; Violet leaf absolute; verbena; vetiver; Juniper berry oil; Wine yeast oil; Wormwood oil; Wintergreen oil; ylang oil; hyssop oil; Civet absolute; cinnamon leaf; Cinnamon bark oil and fractions thereof, or ingredients isolated therefrom;

Individual fragrances from the group of hydrocarbons, such as 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -1,3,5-undecatriene; styrene; diphenylmethane;
the aliphatic alcohols such as hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; 1-octene-3-ol; Mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-Nonadienol; 3,7-dimethyl-7-methoxyoctane-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
the aliphatic aldehydes and their acetals such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; 2-methyloctanal; 2-methyl nonanal; (E) -2-hexenal; (Z) -4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E) -4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10-trimethyl-5,9-undecadienal; Heptanaldiethylacetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; (1-methoxy-propoxy) 1- - 3-ene (E / Z);
the 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-Methylthiohexylacetat; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol;
the aliphatic nitriles such as 2-nonenitrile; 2-Undecensäurenitril; 2-Tridecensäurenitril; 3,12-Tridecadiensäurenitril; 3,7-dimethyl-2,6-octadiensäurenitril; 3,7-dimethyl-6-octensäurenitril;
the ester of aliphatic carboxylic acids such as (E) - and (Z) -3-hexenylformate; ethylacetoacetate; isoamyl; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenylacetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; Butyl butyrate, isoamyl; hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate; hexyl crotonate; Ethylisovalerianat; Ethyl 2-methylpentanoate; ethylhexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; Ethyl (E, Z) -2,4-decadienoate; Methyl-2-octinat; Methyl-2-noninat; Allyl-2-isoamyloxyacetat; Methyl-3,7-dimethyl-2,6-octadienoate, 4-methyl-2-pentyl-crotonate;
the acyclic terpene alcohols such. B. geraniol; nerol; lavandulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octene-2-ol; 2,6-dimethyl octane-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadiene-2-ol; 2,6-dimethyl-3,5-octadiene-2-ol; 3,7-dimethyl-4,6-octadiene-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, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;
the acyclic terpene aldehydes and ketones such. Citronellal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; and the dimethyl and diethyl acetals of Geranial, Neral,
the cyclic terpene alcohols such. Menthol; isopulegol; alpha-terpineol; Terpinenol-4; Menthane-8-ol; Menthane-1-ol; Menthane-7-ol; borneol; soborneol; linalool; monopoly; cedrol; ambrinol; Vetyverol; guaiol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;
the cyclic terpene aldehydes and ketones such. Eg menthone; Isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchon; alpha-ionone; beta-ionone; alpha-n-methylionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-irone; beta-damascenone; 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-methanonaphthalen-8 (5H) -one; 2-methyl-4- (2,6, 6-trimethyl-1-cyclohexen-1-yl) -2-butenal; Nootkatone; Dihydronootkaton; 4,6,8-Mega stigma triene-3-one; alpha-sinensal; beta-Sinensal; acetylated cedarwood oil (methyl cedryl ketone);
the 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-methyl tetrahydro-2H-pyran-4-ol;
the cycloaliphatic alcohols such as alpha, 3,3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-Dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1- (2,2,6-trimethylcyclohexyl) pentan-3-ol; 1- (2,2,6-trimethylcyclohexyl) hexan-3-ol;
the cyclic and cycloaliphatic ethers such as cineole; cedryl methyl ether; Cyclododecyl methyl ether; 1,1-dimethoxycyclododecane; (Ethoxymethoxy) cyclododecane; alpha-Cedrenepoxid; 3a, 6,6,9a-tetramethyl-dodecahydronaphtho [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-cyclohexene-1-yl) -5-methyl-5- (1-methylpropyl) -1,3-dioxane;
the cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert.-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-Dihydro-1,1,2,3,3-pentamethyl-4 (5H) -indanon; 8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone; cyclohexadecanone;
the cycloaliphatic aldehydes such as 2-methyl-4- (2,2,6-trimethyl-cyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexene carbaldehyde;
the cycloaliphatic ketones such. 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-naphtalenylmethylketon; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert-butyl (2,4-dimethyl-3-cyclohexen-1-yl) ketone;
the ester of cyclic alcohols such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthyl acetate, 2-Cyclopentylcyclopentylcrotonat; 3-pentyltetrahydro-2H-pyran-4-yl acetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenyl acetate, respectively; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenylpropionate, respectively; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenyl isobutyrate, respectively; 4,7-Methanooctahydro-5, or 6-indenyl acetate;
the ester of cycloaliphatic alcohols such as 1-cyclohexylethyl crotonate;
the esters of cycloaliphatic carboxylic acids such as. For example, allyl-3-cyclohexylpropionate; Allylcyclohexyloxyacetat; cis- and trans-methyldihydrojasmonate; cis- and trans -methyl-jasmonate; Methyl-2-hexyl-3-oxocyclopentanecarboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; Ethyl-2-methyl-1,3-dioxolan-2-acetate;
the araliphatic alcohols such as benzyl alcohol; 1-phenylethyl; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phenylethyl; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl; 1- (4-isopropylphenyl) ethanol;
the ester of araliphatic alcohols and aliphatic carboxylic acids such as benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-Phenylethylisobutyrat; 2-Phenylethylisovalerianat; 1-phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-Dimethylphenylethylacetat; alpha, alpha-Dimethylphenylethylbutyrat; cinnamyl; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
the araliphatic ethers such as 2-phenylethyl methyl ether; 2-Phenylethylisoamylether; 2-phenylethyl-1-ethoxyethyl ether; phenylacetaldehyde; phenylacetaldehyde; Hydratropaaldehyddimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydroindeno [1,2-d] -m-dioxin; 4,4a, 5,9b-tetrahydro-2,4-dimethylindeno [1,2-d] -m-dioxin;
the aromatic and araliphatic aldehydes such. B. benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; Hydratropaaldehyd; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; 2-methyl-3- (4-isobutylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; cinnamic aldehyde; alpha-Butylzimtaldehyd; alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-Hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3- (4-methoxyphenyl) propanal; 2-methyl-3- (4-methylenedioxyphenyl) propanal;
the aromatic and araliphatic ketones such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthalenyl) ethanone; 2-Benzofuranylethanon; (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) -1H-5-indenyl] ethanone; 8'-hexamethyl-2-acetonaphthone, 5 ', 6', 7 ', 8'-tetrahydro-3', 5 ', 5', 6 ', 8';
the aromatic and araliphatic carboxylic acids and their esters such as benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate; Benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; Phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethylcinnamat; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; benzyl; phenylethyl; Methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenylglycidate; Ethyl-3-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; 3-methyl-5-phenyl-2-pentensäurenitril; 3-methyl-5-phenylpentansäurenitril; methyl anthranilate; Methyl N-methylanthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexene carbaldehyde; 6-Isopropyl; 6-Isobutylchinolin; 6-sec.-butylquinoline; 2- (3-phenylpropyl) pyridine; indole; skatol; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;
the phenols, phenyl ethers and phenyl esters such as estragole; anethole; Eugenylmethylether; isoeugenol; Isoeugenylmethylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-Naphthylisobutylether; 1,4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methyl phenol; 2-ethoxy-5- (1-propenyl) phenol; p-Kresylphenylacetat;
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-dodecanolide; 4-Methyl-1,4-decanolide; 1.15 pentadecanolide; 1,16-hexadecanolide; 9-hexadecene-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide; Ethylene-1,12-dodecanedioate; Ethylene-1,13-tridecandioat; 2,3-dihydrocoumarin; Octahydrocoumarin.

An odorant or flavoring composition according to the invention can be prepared, for example, by providing a component (a) or a mixture of components (a) and (c) and mixing this component or mixture with one or more further odoriferous or aromatic substances (as component ( b)) is mixed. The component (a) is used regularly in an amount sufficient to impart, modify and / or enhance in the finished composition an odor or flavor of the type aldehydic, coniferous, floral, greasy-sweet and / or ozone ,

A fragrance or flavoring composition according to the invention preferably comprises total amount of component (a) in the range from 0.00001 to 99.9% by weight, preferably 0.001 to 70% by weight and particularly preferably 0.01 to 50% by weight, based on the total amount of the fragrance or flavor composition.

If the aldehydes to be used according to the invention or a corresponding mixture are mainly used to impart more (aus) radiation, rounding off and / or harmony to an olfactory or flavoring composition and / or to reinforce certain notes, the total amount of the component is (A) preferably comparatively low and more preferably in the range of 0.01 to 5 wt .-%, preferably in the range of 0.1 to 2 wt .-%, based on the total amount of the fragrance or flavoring composition.

If a comparatively low concentration is selected within the preferred concentration ranges, depending on the other components of the particular composition, in some cases the mediation of the abovementioned odor or taste notes does not yet occur.

The preparation of aldehydes of the type (I) or (II) or corresponding mixtures to be used according to the invention can be carried out by means of known reactions and processes.

For example, analogous to the rules in Journal of Organic Chemistry (1978), 43 (14) 2907 a synthesis of the aldehydes by alkylation of imines and dihydro-1,3-oxazines done.

Alternatively, the aldehydes or aldehyde mixtures to be used according to the invention can be obtained starting from olefins of the following formulas A or B by means of hydroformylation.

Usually, the hydroformylation (oxo synthesis) of a compound A and / or B with synthesis gas (a mixture of carbon monoxide and hydrogen) in the presence of transition metal catalysts (often the VII. Subgroup) is performed. This reaction can be carried out in accordance with hydroformylation reactions of dienes such as n-tetradecene-1. The reaction can be carried out homogeneously or heterogeneously. For the hydroformylation preferably Co or Rh catalysts are used. The hydroformylation of the compound A and / or B according to the invention is preferably based on DE 39 42 954 A1 and DE 43 44 064 carried out.

With regard to the reaction parameters, in particular with regard to preferred catalysts, ligands, solvents or diluents, temperature, pressure, reaction time, homogeneous or heterogeneous reaction, work-up, etc., reference is made to the statements in said publications.

Analogous to DE 39 42 954 A1 can be formed from a compound A and / or B by means of hydroformylation in the presence of a rhodium catalyst such as Rh-2-ethylhexanoate a mixture which in addition to the invention to be used aldehydes also pentadecanal, methyldecylacetaldehyde and / or tridecanal.

Under customary conditions of the preparation (hydroformylation) of aldehydes of the type (I) and / or (II) to be used according to the invention by means of hydroformylation of the corresponding olefins of the above formulas A and / or B, partial migration (isomerization) of the olefinic double bond takes place, so that also the sensorially valuable aldehydes of the type (I) or (II) to be used according to the invention are formed and not only the aldehydes pentadecanal, methyldecylacetaldehyde and / or tridecanal already described with regard to their olfactory properties. Particularly preferred according to the invention is the use of aldehydes of the type (I) and / or (II) whose radical R 'comprises at least two C atoms. A particularly high proportion of the sensory valuable aldehydes of the type (I) or (II) can be z. Example, by a production process in which in a first step terminal olefins are isomerized to internal olefins and in a second step z. B. analog DE 43 44 064 is hydroformylated. Alternatively, the information on production methods can be followed, as described in Fats, soaps, paints (1974), 76 (10), 443-446 ) are described.

If individual aldehydes of the type (I) or (II), ie the aldehydes listed in Table 1, are present in the reaction mixture as a result of the preparation, in particular in addition to further aldehydes and / or pentadecanals, methyldecylacetaldehyde and / or tridecanal to be used according to the invention, their isolation can take place preferably from the reaction mixture by conventional methods such as distillation or rectification. If necessary, a precise separation or far-reaching purification, for example by means of fractionation on a rotating band column, by means of HPLC or preparative gas chromatography.

Fragrance or flavoring compositions of the invention containing aldehydes of type (I) and / or (II) may be used in liquid form, neat or diluted with a solvent for perfuming or flavoring. Suitable solvents for this are e.g. Ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, etc.

Furthermore, odoriferous or flavoring compositions according to the invention containing aldehydes of type (I) and / or (II) may be adsorbed to a carrier which promotes both a fine distribution of the odoriferous or aromatic substances in the product and controlled release the application ensures. Such carriers may be porous inorganic materials such as light sulfate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc. or organic materials such as woods, cellulosic based substances, sugars, dextrins (e.g., maltodextrin), or plastics such as PVC, polyvinyl acetates or polyurethanes. The combination of composition according to the invention and carrier represents an exemplary article according to the invention.

Fragrance or flavoring compositions of the invention containing aldehydes of type (I) and / or (II) may also be microencapsulated, spray dried, as inclusion complexes or as extrusion products (i.e., inventive articles), and in this form e.g. B. to be perfumed or flavored product.

Optionally, 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 release of fragrance, to which end preferably wax-like plastics such as polyvinyl alcohol are used. The resulting products are in turn articles of the invention.

The microencapsulation of the odoriferous or flavoring compositions according to the invention to articles according to the invention can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, e.g. made of polyurethane-like substances or soft gelatin. The spray-dried fragrance or flavoring compositions can be prepared, for example, by spray-drying an emulsion or dispersion containing the fragrance or aroma composition, it being possible to use modified starches, proteins, dextrin and vegetable gums as carriers. Inclusion complexes can be e.g. by incorporating dispersions of the fragrance or flavoring composition and cyclodextrins or urea derivatives into a suitable solvent, e.g. Water, to be produced. Extrusion products may be made by fusing the fragrance or flavor compositions together with a suitable waxy substance and by extrusion followed by solidification, optionally in a suitable solvent, e.g. Isopropanol.

Aldehydes of the type (I) and / or (II) and fragrance or flavor compositions containing compounds of the type (I) and / or (II) can be used in concentrated form, in solutions or in modified form as described above for the Production of perfumed articles according to the invention such. Perfume extractions, eau de parfums, eau de toilettes, shaving waters, eau de colognes, pre-shave products, splash colognes and perfumed towelettes, as well as the perfuming of acidic, alkaline and neutral detergents such as floor cleaners, window glass cleaners, dishwashing detergents , Bath and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam carpet cleaners, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents such as bleach, soak and stain removers, fabric softeners, laundry soap, washing tablets, disinfectants, surface disinfectants and Air fresheners in liquid, gel or solid-applied form, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe creams and personal care products such as solid and liquid soaps, shower gels, shampoos, shaving creams soaps, shaving foams, bath oils, oil-in-water, water-in-oil and water-in-oil-in-water type cosmetic emulsions such as

Skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, Tanning creams and lotions, hair care products such as Hair sprays, hair gels, hair setting lotions, hair lotions, permanent and semi-permanent hair dyes, hair styling agents such as cold waving and hair straightening agents, hair lotions, hair creams and lotions, deodorants and antiperspirants such as hair wipes. Underarm sprays, roll-ons, deodorants, deodorants, decorative cosmetics, e.g. Eyeshadows, nail polishes, make-ups, lipsticks, mascara and candles, lamp oils, incense sticks, insecticides, repellents and fuels.

The aldehydes of type (I) and / or (II) or the corresponding mixtures can be incorporated into flavored or flavored articles, in particular in nutrition, oral hygiene or pleasure preparations.

The diet or pleasure-serving preparations are, for example, baked goods (eg bread, dry biscuits, cakes, other pastry), confectionery (eg chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (eg Coffee, tea, wine, wine-based beverages, beer, beer-based beverages, liqueurs, brandies, brandies, fruit-based sodas, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (eg instant cocoa drinks, Instant tea drinks, instant coffee drinks), meat products (eg ham, fresh sausage or raw sausage preparations, spiced or marinated fresh or salted meat products), eggs or egg products (dry egg, egg whites, egg yolk), cereal products (eg breakfast cereals, muesli bars, pre-cooked wholegrain rice -Products), dairy products (eg milk drinks, milk ice cream, yoghurt, kefir, cream cheese, W eichkäse, hard cheese, dried milk powder, whey, butter, buttermilk, partially or completely hydrolysed milk protein-containing products), products of soy protein or other soybean fractions (eg soymilk and products thereof, soy lecithin-containing preparations, fermented products such as tofu or tempe or products made from them, soy sauces), fruit preparations (eg jams, fruit ice cream, fruit sauces, fruit fillings), vegetable preparations (eg ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, pickled vegetables, cooked vegetables), snacks (eg baked or fried potato chips or potato dough products, bread dough products, corn or peanut based extrudates), fat and oil based products or emulsions thereof (eg mayonnaise, remoulade, dressings, spice preparations), other ready meals and soups (eg dry soups, instant soups, pre-cooked soups), spices , Spice mixtures and in particular seasoning spices (English: Seasonings), which are used for example in the snack area application. After incorporation of the aldehydes of the type (I) and / or (II) or of the corresponding mixtures according to the invention, these preparations are preparations according to the invention (as an example of articles according to the invention).

Formulations according to the invention can be applied, for example, to B. present as a semi-finished product or as seasoning mixture.

Preparations according to the invention can serve, in particular, as semi-finished goods for the production of further preparations for nutrition or enjoyment, in particular in spray-dried form. Compositions according to the invention may also be in the form of capsules, tablets (non-coated and coated tablets, eg enteric coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as pastes or as other swallowing agents. or chewable preparations are present as a dietary supplement.

Oral preparations according to the invention are, in particular, oral and / or dental care products such as toothpastes, tooth gels, tooth powders, mouthwashes, chewing gums and other oral hygiene products.

Other customary active substances, basic substances, auxiliaries and additives for nutrition, oral care or pleasure-use 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 to be included. Furthermore, can the preparations comprise 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.

Preparations according to the invention (as examples of articles according to the invention) containing aldehydes of the type (I) and / or (II) are prepared according to a preferred embodiment by using one or more aldehydes of the type (I) and / or (II) as substance, as Solution (eg in ethanol, water or 1,2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (eg maltodextrin, starch, silica gel), other flavorings or flavorings and optionally further adjuvants and / or stabilizers ( For example, natural or artificial polysaccharides and / or vegetable gums such as modified starches or gum arabic) in a diet, oral care or pleasure serving base preparation are incorporated. Advantageously, preparations according to the invention present as solution and / or suspension or emulsion can also be converted by spray-drying into a solid preparation according to the invention (semi-finished product).

The spray-dried solid preparations according to the invention (as an example of inventive articles) are particularly suitable 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 from 50 to 95% by weight of excipients, in particular maltodextrin and / or starch, from 5 to 40% adjuvants, preferably natural or artificial polysaccharides and / or vegetable gums such as modified starches or gum arabic.

According to a further preferred embodiment, one or more aldehydes of type (I) and / or (II) and optionally other constituents of the preparation according to the invention are initially prepared in emulsions, in liposomes, for example starting from phosphatidylcholine, in microspheres, in nanospheres or also in capsules, granules or extrudates from a suitable for food and luxury food matrix, for example from starch, starch derivatives (eg modified starch), cellulose or cellulose derivatives (eg hydroxypropyl cellulose), other polysaccharides (eg

Dextrin, alginate, curdlan, carrageenan, chitin, chitosan, pullulan), natural fats, natural waxes (e.g., beeswax, carnauba wax), from proteins, e.g. Gelatin or other natural products (e.g., shellac). Depending on the matrix, the products may be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating or other suitable encapsulation processes and optionally a suitable combination of the abovementioned processes. In a further preferred preparation process for a preparation according to the invention, one or more aldehydes of type (I) and / or (II) are first complexed with one or more complexing agents, for example cyclodextrins or cyclodextrin derivatives, preferably .alpha.- or .beta.-cyclodextrin, and in this complexed form used.

Particularly preferred is a preparation according to the invention, wherein the matrix is selected so that one or more aldehydes of the type (I) and / or (II) are released from the matrix delayed, so that a long-lasting effect is achieved. In this respect, a fat, wax, polysaccharide or protein matrix is particularly preferred.

As further constituents for preparations according to the invention which serve nutrition or pleasure, it is possible to use customary bases, auxiliaries and additives for foods or luxury foods, for example water, mixtures of fresh or processed, vegetable or animal raw materials or raw materials (eg raw, roasted , dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or mixtures thereof), digestible or non-digestible carbohydrates (eg sucrose, maltose, fructose , Glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose), sugar alcohols (eg, sorbitol, erythritol), natural or hydrogenated fats (eg, tallow, lard, palm fat, coconut fat, hydrogenated vegetable fat), oils (eg 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, γ-aminobutyric acid, taurine), peptides (eg glutathione), native or processed proteins (eg gelatin), enzymes (eg peptidases), nucleic acids, nucleotides, flavoring agents for unpleasant taste impressions, further taste modulators for further, usually not unpleasant taste impressions, other taste modulating substances (eg inositol phosphate, nucleotides like Guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), emulsifiers (eg lecithins, diacylglycerols, gum arabic), stabilizers (eg carageenan, alginate), preservatives (eg benzoic acid, sorbic acid), antioxidants (eg tocopherol, ascorbic acid), chelators (eg citric acid), organic or inorganic acidulants (eg malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid), bitter substances (eg quinine, caffeine, limonin, amarogentin, humolone, lupolone, catechins, tannins), mineral salts (eg sodium chloride, potassium chloride, Magnesium chloride, sodium ph osphate), the enzymatic browning preventing substances (eg sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or color pigments (eg carotenoids, flavonoids, anthocyanins, chlorophyll and their derivatives), spices, trigeminal active substances or plant extracts containing such trigeminal active substances, synthetic, natural or nature-identical flavorings or fragrances and odorants.

Dental care preparations (preparations for oral care) containing one or more aldehydes of type (I) and / or (II) generally comprise an abrasive system (grinding or polishing agents), such as silicas, calcium carbonates, calcium phosphates, Alumiuniumoxide and / or hydroxylapatites, surface-active substances such as sodium lauryl sulfate, Natriumlaurylsarcosinat and / or Cocamidopropylbetain, humectants such as glycerol and / or sorbitol, thickeners such as carboxymethylcellulose, polyethylene glycols, carrageenan and / or Laponite ^® , sweeteners such as saccharin, flavoring agents for unpleasant taste impressions, Geschmackskorrigemzien for further, 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), cooling agents such eg menthol, menthol derivatives (eg L-menthol, L-menthyl lactate, L-menthyl alkyl carbonates, menthone ketals, menthane carboxylic acid amides), 2,2,2-trialkylacetic acid amides (eg 2,2-diisopropylpropionic acid methylamide), icilin and icilin derivatives, stabilizers and active agents, such as, for example, sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetylpyridinium chloride, aluminum lactate, potassium citrate, potassium nitrate, potassium chloride, strontium chloride, hydrogen peroxide, flavors and / or sodium bicarbonate or odor sclerents.

Chewing gums (as another example of oral care preparations) containing one or more aldehydes of type (I) and / or (II) generally comprise a chewing gum base, i. chewing gum that becomes plastic during chewing, sugar of various types, sugar substitutes, other sweet tasting substances, sugar alcohols, flavoring agents for unpleasant taste impressions, other flavor modulators for further, generally not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or others Substances such as monosodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, flavors and stabilizers or odor remedies.

The preparations according to the invention may preferably also contain an aroma composition in addition to the compound according to the invention in order to round off and refine the taste and / or smell of the preparation. Suitable (additional) flavoring compositions include e.g. synthetic, natural or nature-identical flavorings, fragrances and flavorings as well as suitable excipients and carriers.

The invention will be explained in more detail by way of examples. Unless otherwise indicated, all data are by weight.

Example 1: Preparation of a mixture of aldehydes of the type (I) and (II) (based on the process according to DE 39 42 954 )

In a 1 l stirred autoclave, 420 g of olefin mixture C12 (70%) and C14 (30%), 3.2 g of triphenylphosphine and 2.2 g of a toluene solution of rhodium 2-ethylhexanoate (corresponding to 125 mg of rhodium), respectively a rhodium to phosphorus ratio of 1 to 100 introduced. The mixture was then heated to 130 ° C. within one hour and hydroformylated at this temperature and a pressure of 26 MPa for 6 to 7 hours. After cooling to room temperature, the autoclave was purged with nitrogen. The crude product was filtered (crude yield 442 g) and fractionated on a 30 cm Vigreux column in vacuo.
Yield: 443.5 g (92% of theory) bp .: 130 ° -140 ° C./8 mbar
GC evaluation (20m ZB-WAX, inner diameter 0, 1 8pm / 60-9-220 ° C cold feed system) <b><u> C13 / C15 aldehyde </ u></b> Branching (number of C atoms in residue R ' C13 Area% C15 Area% n- (0) 35.8 11.5 Methyl (1) 24.5 10.3 Ethyl- (2) 5.0 2.2 Propyl- (3) 2.5 1.6 Butyl (4) 1.6 0.9 Pentyl (5) 1.2 0.8 total 70.6 27.3

Example 2: Preparation of a mixture of aldehydes of the type (I) and (II) (based on the process according to DE 43 44 064 )

1. In a 1 l stirred autoclave 420 g of olefin mixture C12 / C14 (olefins of the formula A and / or B) were introduced and heated in the presence of 0.20 g of iron pentacarbonyl for 1 hour at 180 ° C.
2. The resulting olefin isomer was without separation of the isomerization catalyst and after addition of 3.2 g of triphenylphosphine and 2.2 g of a toluene solution of rhodium 2-ethylhexanoate (corresponding to 125 mg of rhodium, corresponding to a rhodium to phosphorus ratio of 1 to 100) for 6 to 7 hours at a temperature of 130 ° C and a pressure of 26 MPa hydroformylated. After cooling to room temperature, the autoclave was purged with nitrogen. The crude product was filtered (crude yield 440 g) and fractionated on a 30 cm Vigreux column in vacuo.
Yield: 433.2 g (89.9% of theory) bp .: 130 ° -140 ° C./8 mbar
GC evaluation (20m ZB-WAX, inner diameter 0, 1 8pm / 60-9-220 ° C cold feed system) <b><u> C13 / C15 aldehyde </ u></b> Branching (number of C atoms in residue R ') C13 Area% C15 Area% n- (0) 5.8 2.2 Methyl (1) 16.4 6.4 Ethyl- (2) 11.5 4.6 Propyl- (3) 10.8 4.3 Butyl (4) 21.1 8.9 Pentyl (5) 13.9 1.4 total 70.5 27.8 The spectroscopic data of prepared C13 and C15 aldehydes were determined. The data is given below.

C13 aldehydes

1. 1. 2-butyl-nonanal
   MS: m / z (%) = 142 (14, M ⁺ - 56), 100 (63), 82 (100), 71 (37), 57 (80), 55 (28), 43 (40), 41 (37).
2. 2. 2-Propyl-decanal
   MS: m / z (%) = 156 (7, M ⁺ - 42), 86 (100), 82 (16), 71 (20), 68 (16), 57 (67), 43 (30), 41 (27).
3. 3. 2-ethyl-undecanal
   MS: m / z (%) = 142 (4, M ⁺ - 56), 85 (8), 72 (100), 57 (31), 55 (12), 43 (22), 41 (17).
4. 4. 2-methyl-dodecanal
   MS: m / z (%) = 156 (3, M ⁺ - 42), 140 (9), 71 (18), 58 (100), 57 (24), 55 (16), 43 (23), 41 (19).
5. 5. Tridecanal
   MS: m / z (%) = 180 (2, M ⁺ - 18), 154 (16), 124 (16), 110 (20), 96 (53), 82 (89), 68 (54), 57 (100), 43 (75).

C15 aldehydes

• 6. 2-Butyl undecanal
  MS: m / z (%) = 182 (19, M ⁺ - 44), 110 (11), 100 (75), 96 (22), 82 (100), 71 (38), 57 (79), 43 (44).
• 7. 2-propyl-dodecanal
  MS: m / z (%) = 184 (4, M ⁺ - 42), 96 (11), 86 (100), 82 (17), 71 (17), 57 (54), 43 (27).
• 8. 2-ethyl-tridecanal
  MS: m / z (%) = 170 (3, M ⁺ - 56), 95 (5), 85 (8), 82 (17), 72 (100), 57 (26), 43 (19).
• 9. 2-methyltetradecanal
  MS: m / z (%) = 168 (9, M ⁺ - 58), 95 (6), 81 (8), 71 (19), 58 (100), 43 (23).
• 10. Pentadecanal
  MS: m / z (%) = 208 (4, M ⁺ - 18), 182 (10), 124 (14), 110 (21), 96 (65), 82 (100), 68 (54), 57 (97), 43 (76).

Example 3: Perfume Composition (Fragrance Composition)

Agrumex LC 10:00 Amarocit® 10% in DPG 10:00 Ambroxide krist. 10:00 basil oil 10:00 Calone 1951 10% in DPG 10:00 cedarwood 10:00 Cedrol Krist 50.00 Citral 10% in DPG 10:00 Citonellol 5:00 coumarin 10:00 Cyclogalbanat® 10% in DPG 15:00 dihydromyrcenol 80.00 Farenal® 10% in DPG 5:00 Galbex 10% in DPG 25.00 Globalide® 80.00 Globanone® 40.00 Hedion 90.00 helional 8:00 pm heliotropin 5:00 Hexenol cis-3 10% in DPG 15:00 Hexenyl salicylate cis-3 10:00 Beta-ionone 5:00 Iso E Super 180.00 Isodamascon® 10% in DPG 10:00 Isomuscone (cyclohexadecanone) 8:00 pm Isoraldein 70 8:00 pm Ketamber 10% in TEC 25.00 Lavandino Grosso Nat. 15:00 lilial 8:00 pm linalool 8:00 pm Linalylacetat 40.00 Mandarin oil brasil. green 50.00 Timberol® 40.00 vanillin 5:00 Veloutone 10% in DPG 8:00 pm Ysamber K® 10:00 total 1000.00

DPG: dipropylene glycol, TEC = triethyl citrate

Odor description of the perfume composition without addition of aldehydes of the type (I) and / or (II): fresh, woody.

In the opinion of the perfumers, this perfume composition becomes fresher, more radiant, more rounded and more harmonious by the addition of 3% by weight of a mixture of aldehydes of types (I) and (II) of Example 2, with an aldehydic, coniferous and sweet note being added the woody and floral aspects are enhanced. The aldehydes used give the composition by their own smell as well as by their modifying and reinforcing effect (booster effect) their own character and connect the different odoriferous elements.

Example 4: Perfume Composition (Fragrance Composition)

Allylcyclohexylpropionat 3:00 amylsalicylate 2:00 benzyl 64.00 Citronellol 122.00 Citral 10% in DPG 2:00 Cyclamenaldehyd 10:00 dihydromyrcenol 3:00 dimethyl benzyl 3:00 Ethyl salicylate 10% in DPG 2:00 eugenol 3:00 Indoflor 10% in DPG 16:00 Galaxolide 50% in DPG 164.00 geraniol 35.00 Dihydromethyljasmonate 6:00 am heliotropin 4:00 hexyl cinnamic aldehyde 121.00 Vertocitral 4:00 Hydroxycitronellal 42.00 indole 2:00 isobutyl 6:00 am Lavandino Grosso Nat. 6:00 am Acetyl 10:00 lilial 190.00 linalool 35.00 Linalylacetat 10:00 Methyl anthranilate 10% in DPG 5:00 nerol 10:00 orange oil 6:00 am Phantolide 4:00 phenylacetaldehyde 6:00 am phenylethyl 75.00 Rosatol 10% in DPG 6:00 am sandalwood 3:00 sandranol 16:00 trifernal 2:00 tonalide 2:00 total 1000.00

DPG: dipropylene glycol

Odor description of the perfume composition without addition of aldehydes of the type (I) and / or (II): flowery, lily-of-the-valley.

In the opinion of the perfumers, this perfume composition comes to life with the addition of 6% by weight of a mixture of aldehydes of the types (I) and (II) from Example 1. The impression of flowery is greatly enhanced. The composition looks radiant, rounded and harmonious, with an aldehydic, coniferous and sweet note added. The aldehydes used give the composition its own character due to its own odor as well as its modifying and strengthening effect (booster effect) and it combines the different odoriferous elements.

Example 5: Shampoo

A mixture of aldehydes of type (I) and / or (II) from Example 1 was incorporated in a dosage of 0.5% by weight into a shampoo base of the following composition: Sodium lauryl ether sulfate
(eg Texapon NSO, Cognis Deutschland GmbH) 12% cocamidopropyl
(eg Dehyton K, Cognis Germany GmbH) 2% sodium chloride 1.4% citric acid 1.3% Phenoxyethanol, methyl, ethyl, butyl, and propylparaben 0.5% water 82.8%

The pH of the shampoo base was about 6. From this, 100 ml of a 20 wt .-% aqueous shampoo solution were prepared. In this shampoo solution, 2 hair slides were washed together for 2 minutes and then under flowing lukewarm water for 20 seconds rinsed. One strand of hair was wet wrapped in aluminum foil and dried the second strand of hair with a hair dryer. Both strands of hair were judged by a panel odor.

Odor description in each case: clear aldehydic note, strongly coniferous note, floral, sweet, ozone.

Example 6: Fabric softener

The perfume composition from Example 3 (after addition of 3% by weight of a mixture of aldehydes of the types (I) and (II) from Example 2) was added in a dosage of 0.5% by weight to a fabric softener base of the following composition incorporated: Quaternary ammonium methosulfate (esterquat), approx. 90%
(eg Rewoquat WE 18, Fa. Witco Surfactants GmbH) 5.5% Alkyldimethylbenzylammonium chloride, approx. 50%
(eg Preventol R50, Fa. Bayer AG) 0.2% Color solution, about 1% -! G 0.3% water 94.0%

The pH of the fabric softener base was in the range of 2 to 3. Two pieces of fabric were mixed with 370 g of a 1% aqueous fabric softener solution based on the 0.5 wt .-% aldehydes of the types (I) and (II ) in a Linetest machine in the softening program 30 minutes at 20 ° C rinsed. The flaps were wrung out and then spun for 20 seconds. A rag was wet-sealed, and one hung up to dry. Subsequently, both flaps were assessed by a panel odor.

Odor description: flowery, woody, fresh, radiant, aldehydic and coniferous aspects with light sweet undertones, rounded and harmonious olfactory impression.

Example 7: Washing powder

The perfume oil composition from Example 4 (after addition of 6% by weight of a mixture of aldehydes of the types (I) and (II) from Example 1) was added in a dosage of 0.4% by weight to a base powder of the following Recipe incorporated: Linear Na-alkylbenzenesulfonate 8.8% Ethoxylated fatty alcohol C12-18 (7 EO) 4.7% Na-soap 3.2% defoamers DOW CORNING (R) 2-4248S POWDERED ANTIFOAM, Silicone oil on zeolite as carrier material 3.9% Zeolite 4A 28.3% Na carbonate 11.6% Na salt of a copolymer of acrylic and maleic acid (Sokalan CP5) 2.4% Na silicate 3.0% carboxymethylcellulose 1.2% Dequest 2066 ([[(phosphonomethyl) imino] bis [(ethylenitrilo) bis (methylene)]] tetrakisphosphonic acid, sodium salt) 2.8% Optical brightener 0.2% Na sulfate 6.5% protease 0.4% sodium perborate 22.0% TAED 1.0%

Two cloths were washed with 370 g of a 1% aqueous Waschpulauge on the basis of 0.4 wt .-% of the perfume oil composition of Example 4 comprising washing powder base (the pH of Waschpulaugeauge is clearly in the basic range) in a Linetest machine washed in the main wash for 45 minutes at 60 ° C. The flaps were first rinsed with cold water for 5 minutes, wrung out and then spun for 20 seconds. A rag was wet-sealed, and one hung up to dry. Subsequently, both flaps were assessed by a panel odor.

Odor description: strongly flowery, radiant, aldehydic and coniferous note with light sweet and woody undertones, rounded and harmonious olfactory impression.

Claims (10)

1. Use of an aldehyde, substituted in the alpha-position by an alkyl radical, of the formula

   

   having

   (I) a total of 13 carbon atoms, wherein
   R denotes an unbranched alkyl radical having 6, 7, 8 or 9 carbon atoms
   and
   R' denotes an unbranched alkyl radical having 2, 3, 4 or 5 carbon atoms,
   or

   (II) a total of 15 carbon atoms, wherein
   R denotes an unbranched alkyl radical having 8, 9, 10 or 11 carbon atoms
   and
   R' denotes an unbranched alkyl radical having 2, 3, 4 or 5 carbon atoms,

   or of a mixture comprising or consisting of two, three or more such aldehydes of type (I) and/or (II),
   as a fragrance or flavouring.
2. Use of an aldehyde, substituted in the alpha-position by an alkyl radical, of the formula

   

   having

   (I) a total of 13 carbon atoms, wherein
   R denotes an unbranched alkyl radical having 6, 7, 8 or 9 carbon atoms
   and
   R' denotes an unbranched alkyl radical having 2, 3, 4 or 5 carbon atoms,
   or

   (II) a total of 15 carbon atoms, wherein
   R denotes an unbranched alkyl radical having 8, 9, 10, 11 or 12 carbon atoms
   and
   R' denotes an unbranched alkyl radical having 1, 2, 3, 4 or 5 carbon atoms,

   or of a mixture comprising or consisting of two, three or more such aldehydes of type (I) and/or (II),
   as a fragrance or flavouring having a coniferous note.
3. Use according to any one of the preceding claims for imparting, modifying and/or enhancing an odour and/or flavour note with the following aspects: aldehydic, coniferous, flowery, fatty-sweet, ozonous.
4. Perfumed or flavoured article comprising (a) an aldehyde, substituted in the alpha-position by an alkyl radical, of the formula

   

   having

   (I) a total of 13 carbon atoms, wherein
   R denotes an unbranched alkyl radical having 6, 7, 8 or 9 carbon atoms
   and
   R' denotes an unbranched alkyl radical having 2, 3, 4 or 5 carbon atoms,
   or

   (II) a total of 15 carbon atoms, wherein
   R denotes an unbranched alkyl radical having 8, 9, 10, 11 or 12 carbon atoms
   and
   R' denotes an unbranched alkyl radical having 1, 2, 3, 4 or 5 carbon atoms,

   or a mixture comprising or consisting of two, three or more such aldehydes of type (I) and/or (II), preferably in an amount that is sufficient to impart, to modify and/or to enhance an odour or flavour note of the aldehydic, coniferous, flowery, fatty-sweet and/or ozonous type,
   and

   (b) one, two, three or more further fragrances or flavourings none of which comprises an aldehyde having 13 or 15 carbon atoms, wherein the further fragrance(s) or flavouring(s) preferably impart a woody and/or flowery odour and/or flavour.
5. Perfumed or flavoured article according to claim 4, comprising

   (c) one, two or all of the aldehydes from the group consisting of pentadecanal, methyl decyl acetaldehyde (2-methyl-dodecanal) and tridecanal.
6. Perfumed or flavoured article according to claim 4 or 5, comprising one, two or more aldehydes of type (I) as well as one, two or more aldehydes of type (II), wherein the weight ratio of the total amount of aldehydes of type (I) to aldehydes of type (II) is in the range from 100:1 to 1:10, preferably in the range from 10:1 to 1:2 and particularly preferably in the range from 8:1 to 1:1.
7. Perfumed or flavoured article according to any one of claims 4 to 6, wherein the article is a fragrance or flavouring composition.
8. Perfumed or flavoured article according to claim 7, characterised in that the fragrance or flavouring composition comprises a total amount of component (a) in the range from 0.00001 to 99.9 wt.%, preferably from 0.001 to 70 wt.% and particularly preferably from 0.01 to 50 wt.%, based on the total amount of the fragrance or flavouring composition.
9. Perfumed or flavoured article according to any one of claims 4 to 6, wherein the article is selected from the group consisting of: perfume extracts, eaux de parfum, eaux de toilette, aftershaves, eaux de cologne, preshave products, splash colognes, perfumed freshening wipes, acid, alkaline and neutral cleaning agents, textile fresheners, ironing aids, liquid detergents, powdered detergents, laundry pretreatment agents, fabric softeners, laundry soaps, laundry tablets, disinfectants, surface disinfectants, air fresheners, aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, aftershave creams and lotions, tanning creams and lotions, hair care products, deodorants and antiperspirants, decorative cosmetics products, candles, lamp oils, incense sticks, insecticides, repellents and fuels.
10. Method of imparting, modifying and/or enhancing an odour or flavour with one, several or all of the following notes: aldehydic, coniferous, flowery, fatty-sweet and ozonous, wherein a sensorially effective amount

    - of an aldehyde, substituted in the alpha-position by an alkyl radical, of the formula

    

    having

    (I) a total of 13 carbon atoms, wherein
    R denotes an unbranched alkyl radical having 6, 7, 8 or 9 carbon atoms
    and
    R' denotes an unbranched alkyl radical having 2, 3, 4 or 5 carbon atoms,
    or

    (II) a total of 15 carbon atoms, wherein
    R denotes an unbranched alkyl radical having 8, 9, 10, 11 or 12 carbon atoms
    and
    R' denotes an unbranched alkyl radical having 1, 2, 3, 4 or 5 carbon atoms,
    or

    - of a mixture comprising or consisting of two, three or more such aldehydes of type (I) and/or (II),
    or

    - of a fragrance or flavouring composition according to either claim 7 or claim 8 comprising such aldehydes,
    is brought into contact or mixed with a product.