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CH635306A5 - Novel perfume - Google Patents

Novel perfume Download PDF

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Publication number
CH635306A5
CH635306A5 CH1200177A CH1200177A CH635306A5 CH 635306 A5 CH635306 A5 CH 635306A5 CH 1200177 A CH1200177 A CH 1200177A CH 1200177 A CH1200177 A CH 1200177A CH 635306 A5 CH635306 A5 CH 635306A5
Authority
CH
Switzerland
Prior art keywords
fragrance
tetramethylhexanal
composition
oil
acetate
Prior art date
Application number
CH1200177A
Other languages
German (de)
Inventor
Erich Dr Klein
Original Assignee
Dragoco Gerberding Co Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dragoco Gerberding Co Gmbh filed Critical Dragoco Gerberding Co Gmbh
Publication of CH635306A5 publication Critical patent/CH635306A5/en

Links

Classifications

    • 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
    • C11B9/0007Aliphatic compounds
    • C11B9/0015Aliphatic compounds containing oxygen as the only heteroatom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/02Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen

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

Description

635 306 635 306

2 2nd

PATENTANSPRÜCHE PATENT CLAIMS

L 2, 3, 5, 5-Tetramethylhexanal. L 2, 3, 5, 5-tetramethylhexanal.

2. Verwendung der Verbindung nach Anspruch 1 als Riechstoff. 2. Use of the compound according to claim 1 as a fragrance.

3. Verwendung nach Anspruch 2 zusammen mit anderen geruchsaktiven Komponenten. 3. Use according to claim 2 together with other odor-active components.

4. Verwendung nach Anspruch 3 in einer Menge von 0,1 bis 10 Gew.-%, insbesondere 0,5 bis 5 Gew.-%, bezogen auf 5 die gesamte Komposition. 4. Use according to claim 3 in an amount of 0.1 to 10 wt .-%, in particular 0.5 to 5 wt .-%, based on 5 of the entire composition.

In der Parfumerie werden seit langer Zeit eine Reihe von aliphatischen, alicyclischen und aromatischen Aldehyden zur Herstellung von Riechstoffkompositionen verwendet. Die zur Anwendung kommenden aliphatischen Aldehyde besitzen in a-Stellung zur Aldehydgruppe meist keine Verzweigung an der Alkylkette. Es sind jedoch einige wenige Ausnahmen bekannt, wie 2-Methylundecanal (Darstellung: Moncrieff, Soap, Perfumery, Cosmetics 1951, 256; s.a. A. Müller, Internationaler Riechstoff-Kodex, Hüthig-Verlag, 1968, S. 223) oder 2-Methyloctanal (A. Müller, Internationaler Riechstoff-Kodex, Hüthig-Verlag, 1968, S. 221), die in a-Stellung eine Methylgruppe besitzen und als Riechstoffe verwendet werden. A number of aliphatic, alicyclic and aromatic aldehydes have long been used in perfumery for the production of fragrance compositions. The aliphatic aldehydes used usually have no branching on the alkyl chain in the a position to the aldehyde group. However, a few exceptions are known, such as 2-methylundecanal (representation: Moncrieff, Soap, Perfumery, Cosmetics 1951, 256; see also A. Müller, Internationaler Riechstoff-Codex, Hüthig-Verlag, 1968, p. 223) or 2-methyloctanal (A. Müller, Internationaler Fragrance Code, Hüthig-Verlag, 1968, p. 221), which have a methyl group in the a position and are used as fragrances.

Es wurde nun gefunden, dass das mehrfach verzweigte 2,3,5,5-Tetramethylhexanal mit der Formel: It has now been found that the multi-branched 2,3,5,5-tetramethylhexanal with the formula:

ein ausgezeichneter neuer Riechstoff ist, der besonders der Kopfnote von blumig riechenden Riechstoffkompositionen natürliche Frische und Ausstrahlung verleiht. is an excellent new fragrance, which gives the top note of floral-smelling fragrance compositions natural freshness and radiance.

Die Herstellung dieses neuen Aldehyds kann auf verschiedenen, an sich bekannten Wegen, z. B. durch Oxidation oder Dehydrierung des entsprechenden 2,3,5,5-Tetramethyl-hexanol, erfolgen. Für die Oxidation sei auf Org. Synth., Coll. Vol. II, 541 verwiesen, wo die Chromsäureoxidation ähnlicher Verbindungen gezeigt ist. The preparation of this new aldehyde can be done in various ways known per se, e.g. B. by oxidation or dehydrogenation of the corresponding 2,3,5,5-tetramethyl-hexanol. For the oxidation, see Org. Synth., Coll. Vol. II, 541 where the chromic acid oxidation of similar compounds is shown.

Für die katalytische Dehydrierung sei verwiesen auf R. Davies und H.H. Hodgson, J. Chem. Soc. London 1943, 282. For the catalytic dehydrogenation, reference is made to R. Davies and H.H. Hodgson, J. Chem. Soc. London 1943, 282.

Der erfindungsgemässe neue Riechstoff kann für sich allein oder insbesondere mit anderen Riechstoffen in verschiedensten Mengenverhältnissen zu neuen Riechstoffkompositionen gemischt werden. Im allgemeinen wird sich jedoch der Anteil des neuen Riechstoffes in der Riechstoffkomposition in den Mengen von 0,1 bis 10, insbesondere 0,5 bis 5 Gew.-%, bezogen auf die gesamte Komposition, bewegen. Derartige Kompositionen können direkt als Parfüm oder auch zur Parfümierung von Kosmetika, Toilettenseifen und Aerosolen usw. dienen. The novel fragrance according to the invention can be mixed on its own or in particular with other fragrances in various proportions to form new fragrance compositions. In general, however, the proportion of the new fragrance in the fragrance composition will range from 0.1 to 10, in particular 0.5 to 5,% by weight, based on the overall composition. Such compositions can be used directly as perfume or also for perfuming cosmetics, toilet soaps and aerosols etc.

Die nachfolgenden Beispiele erläutern die Erfindung. The following examples illustrate the invention.

Beispiel 1 Parfümkomposition mit Rosenduft Example 1 Perfume composition with rose scent

20 Nonanal 10%ig 10 g 20 nonanal 10% 10 g

4-Methyl-2-isobutenyltetrahydropyran 10%ig 10 g 4-methyl-2-isobutenyltetrahydropyran 10% 10 g

Undecylenaldehyd 10g Undecylenaldehyde 10g

Phenyläthylacetat 25 g Phenylethyl acetate 25 g

Guajakholzöl 30 g Guaiac wood oil 30 g

25 Citronellylacetat 30 g 25 citronelly acetate 30 g

Methylionon 40 g Methyl ionone 40 g

Geraniumöl Bourbon 50 g Geranium oil bourbon 50 g

Trichlormethyl-phenyl-carbinylacetat 80 g Trichloromethyl-phenyl-carbinyl acetate 80 g

Geraniol 219 g Geraniol 219 g

30 Phenyläthylalkohol 235 g 30 phenylethyl alcohol 235 g

Citronellol 260 g Citronellol 260 g

999 g 999 g

2,3,5,5-Tetramethylhexanal 1 g 2,3,5,5-tetramethylhexanal 1 g

1000 g 1000 g

Der Zusatz des neuen Aldehyds verleiht der Komposition eine natürliche blumige Frische. The addition of the new aldehyde gives the composition a natural floral freshness.

Beispiel 2 Parfümkomposition mit Apfelduft Example 2 Perfume composition with apple fragrance

Bergamottöl 190 g Bergamot oil 190 g

45 Octylaldehyd-dimethylacetal 150 g 45 octyl aldehyde dimethyl acetal 150 g

Hydroxycitronellal-dimethylacetal 180 g a-Hexylzimtaldehyd 70 g Hydroxycitronellal dimethylacetal 180 g a-hexyl cinnamaldehyde 70 g

Nerol 60 g Nerol 60 g

Phenyläthylalkohol 50 g Phenylethyl alcohol 50 g

50 Galbanum Extrakt 50 g 50 galbanum extract 50 g

Nerylacetat 40 g Nerylacetate 40 g

Phenyläthylacetat 30 g Phenyl ethyl acetate 30 g

AldehydC 10 1% 25 g AldehydeC 10 1% 25 g

Undecylenaldehyd 10%ig 25 g Undecylenaldehyde 10% 25 g

4-tert. Butylcyclohexylacetat 20 g 4-tert. Butylcyclohexyl acetate 20 g

Patchouliöl 20 g Patchouli oil 20 g

Styrollylacetat 20 g Styrene acetate 20 g

Phenyläthylacetat 15 g Phenyl ethyl acetate 15 g

Cedernblätteröl 5 g Cedar leaf oil 5 g

60 - 60 -

950 g 950 g

2,3,5,5-Tetramethylhexanal 50 g 2,3,5,5-tetramethylhexanal 50 g

1000 g 1000 g

65 Der Zusatz von 2,3,5,5-Tetramethylhexanal bewirkt die Verstärkung des Duftes der Komposition nach frischen, reifen Äpfeln, wobei eine besondere natürliche Abrundung bemerkbar ist. 65 The addition of 2,3,5,5-tetramethylhexanal increases the fragrance of the composition of fresh, ripe apples, with a special natural rounding being noticeable.

3 3rd

635 306 635 306

Beispiel 3 Blumige Phantasienote Example 3 Flowery fantasy note

Phenyläthylalkohol Phenylethyl alcohol

180 g 180 g

Citronellol Citronellol

100 g a-Hexylzimtaldehyd 100 g of a-hexyl cinnamaldehyde

100 g 100 g

Vetiverylacetat Vetiveryl acetate

80 g 80 g

Moschus Keton Musk ketone

90 g 90 g

Methyljonon Methyl ionone

100 g 100 g

Ylang-Ylang-Öl Ylang-ylang oil

60 g 60 g

Hydroxycitronellal Hydroxycitronellal

60 g 60 g

Benzylsalicylat Benzyl salicylate

60 g 60 g

Amylsalicylat Amyl salicylate

40 g 40 g

Orangenöl Orange oil

35 g 35 g

Sandelholzöl Sandalwood oil

30 g 30 g

Nerolidol Nerolidol

20 g 20 g

Eugenol Eugenol

10g 10g

Beta-Iron Beta iron

10 g 10 g

Styrolylacetat Styrolylacetate

10g y-Undecalakton 10g y-undecalactone

5g 5g

990 g 990 g

2,3,5,5-Tetramethylhexanal 2,3,5,5-tetramethylhexanal

10 g 10 g

1000 g 1000 g

Der Zusatz von 2,3,5,5-Tetramethylhexanal verstärkt in olfaktorisch relevanter Weise die natürliche blumige Kopfnote der Komposition. The addition of 2,3,5,5-tetramethylhexanal enhances the natural floral top note of the composition in an olfactory manner.

CH1200177A 1977-05-25 1978-01-01 Novel perfume CH635306A5 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19772723636 DE2723636C3 (en) 1977-05-25 1977-05-25 2,3,5,5-tetramethylhexanal and its use as a fragrance

Publications (1)

Publication Number Publication Date
CH635306A5 true CH635306A5 (en) 1983-03-31

Family

ID=6009846

Family Applications (1)

Application Number Title Priority Date Filing Date
CH1200177A CH635306A5 (en) 1977-05-25 1978-01-01 Novel perfume

Country Status (6)

Country Link
JP (1) JPS53147016A (en)
CH (1) CH635306A5 (en)
DE (1) DE2723636C3 (en)
FR (1) FR2391986A1 (en)
GB (1) GB1539310A (en)
NL (1) NL7709406A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4420423A (en) * 1980-10-09 1983-12-13 International Flavors & Fragrances Inc. Methyl substituted-2-oxohexane derivatives and process for preparing and using same
DE3169359D1 (en) * 1980-06-19 1985-04-25 Int Flavors & Fragrances Inc Olefin dimers, derivatives thereof and organoleptic uses thereof
US4421679A (en) * 1980-10-09 1983-12-20 International Flavors & Fragrances Inc. Methyl substituted-2-oxohexane derivatives and processes for preparing and using same
DE3622600A1 (en) * 1986-07-05 1988-01-14 Basf Ag NEW ALIPHATIC ALDEHYDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A FRAGRANCE
US5066641A (en) * 1990-09-27 1991-11-19 International Flavors & Fragrances Inc. 3,5,5-trimethylhexanal oxime and organoleptic uses thereof
DE10110858A1 (en) * 2001-03-07 2002-09-12 Cognis Deutschland Gmbh 2,3,5,5-tetramethylhexanal derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH478909A (en) * 1966-08-03 1969-09-30 Givaudan & Cie Sa Fragrance compositions

Also Published As

Publication number Publication date
NL7709406A (en) 1978-11-28
FR2391986A1 (en) 1978-12-22
DE2723636B2 (en) 1980-07-31
DE2723636A1 (en) 1978-12-07
JPS53147016A (en) 1978-12-21
DE2723636C3 (en) 1981-07-09
GB1539310A (en) 1979-01-31

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