EP2772527B1 - Neuartige Decenalmischungen und ihre Verwendung in Parfümzusammensetzungen - Google Patents

Neuartige Decenalmischungen und ihre Verwendung in Parfümzusammensetzungen Download PDF

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Publication number
EP2772527B1
EP2772527B1 EP13157316.4A EP13157316A EP2772527B1 EP 2772527 B1 EP2772527 B1 EP 2772527B1 EP 13157316 A EP13157316 A EP 13157316A EP 2772527 B1 EP2772527 B1 EP 2772527B1
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EP
European Patent Office
Prior art keywords
enal
dec
fragrance
mixture
fragrance formulation
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Application number
EP13157316.4A
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English (en)
French (fr)
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EP2772527A1 (de
Inventor
Anubhav P.S. Narula
Edward Mark Arruda
Franc T. Schiet
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
International Flavors and Fragrances Inc
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International Flavors and Fragrances Inc
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Priority to ES13157316.4T priority Critical patent/ES2550087T3/es
Priority to EP13157316.4A priority patent/EP2772527B1/de
Publication of EP2772527A1 publication Critical patent/EP2772527A1/de
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Publication of EP2772527B1 publication Critical patent/EP2772527B1/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom

Definitions

  • the present invention relates to novel decenal mixtures and the incorporation and use of these mixtures as fragrance materials.
  • fragrance industry There is an ongoing need in the fragrance industry to provide chemicals with strong odors so that less fragrance is needed to accomplish the desired odor effect. This, therefore, gives perfumers and other persons the freedom to create new fragrances for perfumes, colognes and personal care products without the limitation of cost.
  • practical considerations such as the scale of synthesis operation may also determine the applicability of identified fragrance molecules in commercial use. However, whether the production of a given fragrance molecule can be carried out at a commercial scale is sometimes unpredictable. For these reasons, continuous effort has been made in fragrance industry to investigate and develop economical processes for making fragrance molecules that possess high strength.
  • EP2 008 637 is a patent application which describes malodor counteracting (MOC) compositions which contain aliphatic aldehyde, aliphatic ketone and primary alcohol.
  • MOC malodor counteracting
  • Dec-6-enal is identified as a flavorant in dry parsley ( See, Masanetz et al. 1998. Flavor and Fragrance Journal, Vol.13:2, pp 115-124 ). Dec-7-enal is employed to reduce the alcohol odor and alcohol sting, but it acts differently from a traditional perfume, wherein a traditional perfume overpowers the alcohol odor or sting by making compositions smell like the perfume ( See , U.S. Patent No. 5,843,881 ). Dec-8-enal falls under a generic structure that is disclosed as having potential fragrance use ( See , U.S. Publication No. 2011/0142776 ). However, the generic structure as taught covers a wide range of compounds and the synthetic method as described cannot lead to the synthesis of dec-8-enal.
  • dec-6-enal, dec-7-enal, and dec-8-enal were each individually reported since early 1990's with various flavor and fragrance properties. They were extracted from natural resources or synthesized via methods that required multi-steps and suffered from long reaction times leading to complex and expensive procedures. To date, none of dec-6-enal, dec-7-enal, and dec-8-enal has achieved commercial importance as a fragrance material. More importantly, nothing set forth in the prior art discloses a mixture of dec-6-enal, dec-7-enal, and dec-8-enal having specified ratios.
  • the present invention has discovered a convenient and economical process that provides a novel mixture of dec-6-enal, dec-7-enal, and dec-8-enal.
  • the present invention has further surprisingly and unexpectedly discovered that this novel decenal mixture, only when in specified mixing ratios, possesses desirable fragrance properties of high strength that are suitable for fragrance application.
  • the present invention provides a fragrance formulation in accordance with claim 1 herein.
  • the present invention provides a novel decenal mixture and its unexpected advantageous use in enhancing, improving or modifying the fragrance of perfumes, colognes, toilet water, fabric care products, personal products and the like.
  • novel decenal mixture contains decenals that are represented by Formula I set forth below: wherein the broken line represents one double bond and two single bonds.
  • Another embodiment of the present invention relates to a method of improving, enhancing or modifying a fragrance formulation through the addition of an olfactory acceptable amount of a mixture in accordance with claim 7 herein.
  • decenals of the present invention may be represented by the following structures:
  • Formula II is dec-6-enal
  • Formula III is dec-7-enal
  • Formula IV is dec-8-enal.
  • the present invention relates to a mixture of dec-6-enal (8-22% by weight), dec-7-enal (20-43%), and dec-8-enal (35-59%) that possesses desirable and useful fragrance properties.
  • the decenals of the present invention can be prepared from 9-decenol (Rosalva, commercially available at International Flavors & Fragrances Inc.) according to the reaction scheme below, the details of which are specified in the Examples. Materials were purchased from Aldrich Chemical Company unless noted otherwise.
  • the isomeric products obtained as described above can be further separated using techniques known to those with skill in the art. Suitable techniques include, for example, distillation and chromatography such as high performance liquid chromatography, referred to as HPLC, particularly silica gel chromatograph, and gas chromatography trapping known as GC trapping. Yet, commercial products are mostly offered as isomeric mixtures.
  • HPLC high performance liquid chromatography
  • silica gel chromatograph particularly silica gel chromatograph
  • GC trapping gas chromatography trapping
  • commercial products are mostly offered as isomeric mixtures.
  • the use of the decenal mixtures of the present invention is widely applicable in current perfumery products, including the preparation of perfumes and colognes, the perfuming of personal care products such as soaps, shower gels, and hair care products, fabric care products, air fresheners, and cosmetic preparations.
  • the present invention can also be used to perfume cleaning agents, such as, but not limited to detergents, dishwashing materials, scrubbing compositions, window cleaners and the like.
  • the decenal mixtures of the present invention can be used alone or in combination with other perfuming compositions, solvents, adjuvants and the like.
  • the nature and variety of the other ingredients that can also be employed are known to those with skill in the art.
  • Many types of fragrances can be employed in the present invention, the only limitation being the compatibility with the other components being employed. Suitable fragrances include but are not limited to fruits such as almond, apple, cherry, grape, pear, pineapple, orange, strawberry, raspberry; musk, flower scents such as lavender-like, rose-like, iris-like, carnation-like. Other pleasant scents include herbal and woodland scents derived from pine, spruce and other forest smells. Fragrances may also be derived from various oils, such as essential oils, or from plant materials such as peppermint, spearmint and the like.
  • fragrances A list of suitable fragrances is provided in US Pat. No. 4,534,891 . Another source of suitable fragrances is found in Perfumes, Cosmetics and Soaps, Second Edition, edited by W. A. Poucher, 1959 .
  • the fragrances provided in this treatise are acacia, cassie, chypre, cyclamen, fern, gardenia, hawthorn, heliotrope, honeysuckle, hyacinth, jasmine, lilac, lily, magnolia, mimosa, narcissus, freshly-cut hay, orange blossom, orchid, reseda, sweet pea, trefle, tuberose, vanilla, violet, wallflower, and the like.
  • the decenal mixtures of the present invention can be used in combination with a complementary fragrance compound.
  • complementary fragrance compound as used herein is defined as a fragrance compound selected from the group consisting of 2-[(4-methylphenyl)methylene]-heptanal (Acalea), iso-amyl oxyacetic acid allylester (Allyl Amyl Glycolate), (3,3-dimethylcyclohexyl)ethyl ethyl propane-1,3-dioate (Applelide), (E/Z)-1-ethoxy-1-decene (Arctical), 2-ethyl-4-(2,2,3-trimethyl 3-cyclo-penten-1-yl)-2-buten-1-ol (Bacdanol), 2-methyl-3-[(1,7,7-trimethylbicyclo[2.2.1]hept-2-yl)oxy] exo-1-propanol (Bornafix), 1,2,3,5,6,7-hex
  • fragrance formulation means the same and refer to a consumer composition that is a mixture of compounds including, for example, alcohols, aldehydes, ketones, esters, ethers, lactones, nitriles, natural oils, synthetic oils, and mercaptans, which are admixed so that the combined odors of the individual components produce a pleasant or desired fragrance.
  • the fragrance formulation of the present invention is a consumer composition comprising the decenal mixtures of the present invention.
  • the fragrance formulation of the present invention comprises the decenal mixtures of the present invention and further a complementary fragrance compound as defined above.
  • fragrance product means a consumer product that adds a fragrance or masks a malodor. Fragrance products may include, for example, perfumes, colognes, personal care products such as soaps, shower gels, and hair care products, fabric products, air fresheners, cosmetic preparations, and perfume cleaning agents such as detergents, dishwashing materials, scrubbing compositions, and window cleaners.
  • the fragrance product of the present invention is a consumer product that contains the decenal mixtures of the present invention.
  • the fragrance product of the present invention contains the decenal mixtures of the present invention and further a complementary fragrance compound as defined above.
  • the term “improving” in the phrase “improving, enhancing or modifying a fragrance formulation” is understood to mean raising the fragrance formulation to a more desirable character.
  • the term “enhancing” is understood to mean making the fragrance formulation greater in effectiveness or providing the fragrance formulation with an improved character.
  • the term “modifying” is understood to mean providing the fragrance formulation with a change in character.
  • Olfactory acceptable amount is understood to mean the amount of compound in perfume compositions the individual component will contribute to its particular olfactory characteristics, but the olfactory effect of the perfume composition will be the sum of the effects of each of the perfumes or fragrance ingredients.
  • the decenal mixtures of the invention can be used to alter the aroma characteristics of the perfume composition, or by modifying the olfactory reaction contributed by another ingredient in the composition.
  • the amount will vary depending on many factors including other ingredients, their relative amounts and the effect that is desired.
  • the amount of the decenal mixtures of the present invention employed in a fragrance formulation varies from about 0.005 to about 70 weight percent, preferably from 0.005 to 50 weight percent, more preferably from 0.5 to 25 weight percent, and even more preferably from 1 to 10 weight percent.
  • Those with skill in the art will be able to employ the desired amount to provide desired fragrance effect and intensity.
  • other materials can also be used in conjunction with the fragrance formulation.
  • Well known materials such as surfactants, emulsifiers, polymers to encapsulate the fragrance can also be employed without departing from the scope of the present invention.
  • fragrance formulation When used in a fragrance formulation these ingredients provide powerful, clean, aldehydic, crispy, green, ambrette seed like, sweet, bright, and melon notes to make the fragrance formulation more desirable and noticeable, and add the perception of value.
  • the odor qualities found in this material assist in beautifying and enhancing the finished accord as well as improving the performance of the other materials in the fragrance.
  • 6,7,8-Decene-1ol was described as having aldehydic, green, floral, rosy, and waxy notes.
  • Dec-6-enal, Dec-7-enal, and Dec-8-enal Mixture of Different Ratios The decenal mixture (synthesized as above in EXAMPLE II) was further carefully distilled through a GOODLOE column with high theoretical plates to afford a series of decenal mixture of different mixing ratios.
  • fragrance formula exemplified as follows demonstrated that the addition of the mixture of dec-6-enal (22%), dec-7-enal (43%), and dec-8-enal (35%) (Sample 7 as described in EXAMPLE III) provided clean, aldehydic, crispy, green, ambrette seed-like, and slightly sweet characters to the fragrance formula.
  • Benzophenone 100 Cinnamic Alcohol 50 Damascone, Delta 5 Decanol, n- 30 Dimethyl Benzyl Carbinyl Acetate 50 Diphenyl Oxide 20 Dodecanol, n- 15 Ethyl Methyl Phenyl Glycidate 5 Eugenol 10 Geraniol 60 Guaiacwood Oil 20 Ionone Alpha 10 Iso E Super® 60 Methyl Ionone Gamma 65 Octanol, n- 10 Phenoxanol ® 200 Phenyl Acetaldehyde Dimethyl Acetal 7 Phenyl Ethyl Alcohol 100 Phenyl Methyl Carbinyl Acetate 20 Rose Oxide 5 Vertenex ® 150 Decenal Mixture (Sample 7) 8 Total 1000

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Claims (10)

  1. Eine Duftrezeptur bestehend aus einem Gemisch aus Dec-6-enal, Dec-7-enal und Dec-8-enal, wobei das Gemisch 8-22 Gew.-% Dec-6-enal, 20-43 Gew.-% Dec-7-enal und 35-59 Gew.-% Dec-8-enal enthält.
  2. Die Duftrezeptur in Anspruch 1, eingebunden in ein Produkt ausgewählt aus der Gruppe bestehend aus einem Parfüm, einem Kölnischwasser, einem Eau de Toilet, einem kosmetischen Produkt, einem Körperpflegeprodukt, einem Hautpflegeprodukt, einem Reinigungsprodukt und einem Lufterfrischer.
  3. Die Duftrezeptur in Anspruch 2, wobei das Reinigungsprodukt ausgewählt ist aus der Gruppe bestehend aus einem Waschmittel, einer Spülmittelzusammensetzung, einer Scheuermittelverbindung und einem Fensterreiniger.
  4. Die Duftrezeptur in Anspruch 2 oder Anspruch 3, wobei das Gemisch in einer Menge von 0,005 bis 50 Gew.-% des Produkts enthalten ist.
  5. Die Duftrezeptur in Anspruch 2 oder Anspruch 3, wobei das Gemisch in einer Menge von 0,5 bis 25 Gew.-% des Produkts enthalten ist.
  6. Die Duftrezeptur in Anspruch 2 oder Anspruch 3, wobei das Gemisch in einer Menge von 1 bis 10 Gew.-% des Produkts enthalten ist.
  7. Ein Verfahren zur Verbesserung, Verstärkung oder Veränderung einer Duftrezeptur durch Hinzufügung einer olfaktorisch akzeptablen Menge eines Gemisches aus Dec-6-enal, Dec-7-enal und Dec-8-enal, wobei das Gemisch 8-22 Gew.-% Dec-6-enal, 20-43 Gew.-% Dec-7-enal und 35-59 Gew.-% Dec-8-enal enthält.
  8. Das Verfahren in Anspruch 7, wobei die olfaktorisch akzeptable Menge zwischen 0,005 und 50 Gew.-% der Duftrezeptur liegt.
  9. Das Verfahren in Anspruch 7, wobei die olfaktorisch akzeptable Menge zwischen 0,5 und 25 Gew.-% der Duftrezeptur liegt.
  10. Das Verfahren in Anspruch 7, wobei die olfaktorisch akzeptable Menge zwischen 1 und 10 Gew.-% der Duftrezeptur liegt.
EP13157316.4A 2013-02-28 2013-02-28 Neuartige Decenalmischungen und ihre Verwendung in Parfümzusammensetzungen Active EP2772527B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
ES13157316.4T ES2550087T3 (es) 2013-02-28 2013-02-28 Mezclas de decenal novedosas y su uso en composiciones de perfume
EP13157316.4A EP2772527B1 (de) 2013-02-28 2013-02-28 Neuartige Decenalmischungen und ihre Verwendung in Parfümzusammensetzungen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP13157316.4A EP2772527B1 (de) 2013-02-28 2013-02-28 Neuartige Decenalmischungen und ihre Verwendung in Parfümzusammensetzungen

Publications (2)

Publication Number Publication Date
EP2772527A1 EP2772527A1 (de) 2014-09-03
EP2772527B1 true EP2772527B1 (de) 2015-09-16

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ID=47877805

Family Applications (1)

Application Number Title Priority Date Filing Date
EP13157316.4A Active EP2772527B1 (de) 2013-02-28 2013-02-28 Neuartige Decenalmischungen und ihre Verwendung in Parfümzusammensetzungen

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EP (1) EP2772527B1 (de)
ES (1) ES2550087T3 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6675036B1 (ja) * 2018-12-21 2020-04-01 高砂香料工業株式会社 香料組成物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4534891A (en) 1982-11-12 1985-08-13 International Flavors & Fragrances Inc. Branched C13 -alk-1-en-5-ones and use thereof in perfumery
US5843881A (en) 1997-02-13 1998-12-01 The Procter & Gamble Company Spray compositions
DE10152992A1 (de) 2001-10-26 2003-05-08 Haarmann & Reimer Gmbh Gemische zur Verwendung als Moschusriechstoff
DE112007000301B4 (de) 2006-02-07 2015-05-21 Symrise Ag Mischungen ungesättigter makrocyclischer Epoxide als Riechstoffe
WO2008155683A1 (en) * 2007-06-18 2008-12-24 Firmenich Sa Malodor counteracting compositions and method for their use
US8557262B2 (en) 2008-09-12 2013-10-15 Firmenich Sa Divinyl ether derivatives capable of releasing active aldehydes and ketones and methods of use for perfuming surfaces

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Publication number Publication date
ES2550087T3 (es) 2015-11-04
EP2772527A1 (de) 2014-09-03

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