EP1174117B1 - Eine Mischung von Nitrilen enthaltende Riechstoffzusammensetzung - Google Patents

Eine Mischung von Nitrilen enthaltende Riechstoffzusammensetzung Download PDF

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Publication number
EP1174117B1
EP1174117B1 EP20010116983 EP01116983A EP1174117B1 EP 1174117 B1 EP1174117 B1 EP 1174117B1 EP 20010116983 EP20010116983 EP 20010116983 EP 01116983 A EP01116983 A EP 01116983A EP 1174117 B1 EP1174117 B1 EP 1174117B1
Authority
EP
European Patent Office
Prior art keywords
undecenonitrile
fragrance composition
composition according
mixture
fragrance
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
EP20010116983
Other languages
English (en)
French (fr)
Other versions
EP1174117A1 (de
Inventor
Markus Gautschi
Pierre Bachmann
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.)
Givaudan SA
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Givaudan SA
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Filing date
Publication date
Priority claimed from EP00115699A external-priority patent/EP1174116A1/de
Application filed by Givaudan SA filed Critical Givaudan SA
Priority to EP20010116983 priority Critical patent/EP1174117B1/de
Publication of EP1174117A1 publication Critical patent/EP1174117A1/de
Application granted granted Critical
Publication of EP1174117B1 publication Critical patent/EP1174117B1/de
Anticipated expiration legal-status Critical
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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
    • C11B9/0023—Aliphatic compounds containing nitrogen as the only heteroatom

Definitions

  • the present invention relates to fragrance compositions comprising a mixture of (9E)-undecenonitrile, (9Z)-undecenonitrile and 10-undecenonitrile, their use as well as a method for preparing scented consumer products containing said mixture.
  • Aldehydes with hesperidic and floral notes are important perfumery ingredients. Examples for such aldehydes are e.g. octanal, nonanal, decanal, undecanal, 10-undecenal and citral. However, these aldehydes are readily affected under oxidizing conditions or solutions having a pH lower than 5 or higher than 9. Under these conditions the above mentioned aldehydes are chemically modified and therefore loose their fragrance characteristics and/or generate additional off notes. Nitriles such as (9E)-undecenonitrile (1) (9Z)-undecenonitrile (2) and 10-undecenonitrile (3) are already described in literature. Zhu et al.
  • nitriles such as decanonitrile, dodecanonitrile, tetrahydrogeranonitrile, Geranonitrile (3,7-dimethyl-2,6-octadienenitrile) and Lemonile® (3,7-dimethyl-2(3),6-nonadienenitrile) is established in perfumery.
  • These compounds are less affected under strong acid, basic and/or oxidizing conditions than aldehydes and they exhibit aldehydic and hesperidic notes with floral aspects which are similar to those of the above mentioned aldehydes.
  • a harsh, metallic odor appears as concomitant of theses nitriles, which confers a "synthetic" and "dirty, fatty" aspect to the compositions they are applied to.
  • An object of the present invention is to provide a fragrance composition which has a fresh sparkling, floral, fruity and warm odor and a high stability under aggressive alkaline conditions.
  • fragrance composition which has a fresh sparkling, floral, fruity and warm odor and a high stability under aggressive acidic conditions.
  • the present invention relates to a fragrance composition
  • a fragrance composition comprising a mixture of (9E)-undecenonitrile, (9Z)-undecenonitrile and 10-undecenonitrile.
  • the mixture comprised in the fragrance composition of the present invention as well as the fragrance composition according to the present invention may be used alone or in combination with numerous fragrance ingredients of natural and/or synthetic origin.
  • the range of the natural fragrances includes in addition to volatile, also moderately and only slightly volatile components.
  • the synthetic fragrance ingredients belong to practically all classes of fragrant substances. Examples for such natural and synthetic ingredients are listed e.g. in "Perfume and Flavor Materials of Natural Origin", S. Arctander, Ed., Elizabeth, N.J., 1960 and “Perfume and Flavor Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994.
  • a fragrance ingredient is defined as a substance with olfactory characteristics.
  • Such an additional fragrance ingredient may consist of one or several ingredients.
  • the compositions of the present invention harmonize particularly well with additional fragrance ingredients such as fresh, hesperidic notes (lemon, mandarin, etc.), fruity accords (peach, apricot, etc.), floral notes (lily of the valley, rose, iris, jasmine, ylang-ylang, narcissus notes, etc.), green and agrestic notes (galbanum, tagete, lavender, thyme, ect).
  • (9E)-undecenonitrile is the major compound in these mixture comprised in the fragrance composition according to the present invention, comprising more than 30% by weight of it.
  • the said mixture comprises between about 30% and about 80% of (9E)-undecenonitrile, more preferably between about 40% and about 60%.
  • 10-undecenonitrile is the minor component in said mixture, comprising less than 40% by weight of it.
  • said mixture comprises 10-undecenonitrile between about 0.01% and about 30%, more preferably between 5% and 20%.
  • compositions of the present invention are excellent for use in any field of perfumery, especially in functional perfumery.
  • Consumer products with a non-hostile or a hostile medium comprising a fragrant composition according to the present invention as well as an additional ingredient are preferred.
  • Consumer products with a non-hostile media include alcoholic solutions, shampoos, hair conditioners, bath oils, air freshners, cosmetics and skin care products.
  • Consumer products with aggressive alkaline media include soaps, laundry detergents, bleaches, automatic dishwashing powders, scouring powders.
  • Consumer products with aggressive acidic media include fabric softeners, deodorants, antiperspirants and cleaners containing citric acid, hydrochloric acid, sulfonic acid or phosphoric acid.
  • Consumer products with aggressive oxidizing media include hair colorants and bleaches.
  • compositions of the present invention varies depending on the nature of the product, and the intensity of the desired odor. These factors are known to those skilled in the art.
  • compositions of the present invention are present in the range of 0.01% to 1% in the product.
  • compositions of the present invention can be used in a variety of cleansing products for household and commercial applications, including bleaches, laundry detergents, dishwasher detergents, stain removers, scouring agents, fabric softeners, soaps, all purpose and special cleaners, in various forms including liquids, gels, sprays, bars sticks and powders.
  • the fragrance compositions according to the present invention can be obtained either by a one-pot reaction from a mixture of the corresponding aldehydes or by mixing the purified nitriles (1)-(3), obtained from the pure corresponding aldehydes. It is not necessary but possible to purify the aldehyde mixture before starting the one-pot reaction.
  • the scented consumer products for functional perfumery are prepared by admixing the mixture of (9E)-undecenonitrile, (9Z)-undecenonitrile and 10-undecenonitrile, other optional fragrance ingredients, liquid and/or solid ingredients as well as a medium.
  • the present invention refers in a further aspect to a method for preparing scented consumer products for functional perfumery by admixing the mixture of (9E)-undecenonitrile, (9Z)-undecenonitrile and 10-undecenonitrile obtained by a one-pot reaction, another optional fragrance ingredient, liquid and/or solid ingredients as well as a medium.
  • the reaction flask is charged with acetic anhydride (612 g, 6 mol) and heated to 120°C.
  • a solution of (E,Z)-9-undecenal oxime (225 g, 1.2 mol) in toluene (890 ml) is added slowly over a period of 2.5 h.
  • the reaction mixture is kept at reflux temperature for 4 h, cooled to room temperature and diluted with hexane (600 ml).
  • the organic solution is washed 3x with H 2 O (800 ml each), 3x with 5N NaOH (300 ml each) and 3x with brine (600 ml each), dried over MgSO 4 and concentrated in vacuo to give a yellowish oil (217 g).
  • the odor of both solutions were then evaluated by a panel of 14 perfumers. Both solutions were then divided into two aliquots, which were stored for 1 month at 4° C (samples II and V) and 37° C (samples III and VI), respectively. All solutions were then again assessed olfactorily by a panel of 14 perfumers.
  • Citrus fragrance composition for a bleach containing consumer product Ingredients Parts per weight (+) (-) Agrumex 14.0 14.0 Amberketal, 10% in IPM 0.4 0.4 Ambrofix 0.4 0.4 Clonal 2.0 2.0 Cumin nitrile 0.1 0.1 Damascone alpha 0.4 0.4 Dihydromyrcenol 25.0 25.0 Diphenyl oxide 10.0 10.0 Dipropylene glycol 24.0 25.0 Ethyl vanilline 0.4 0.4 Eucalyptol 3.0 3.0 Fenchyl alcohol 0.5 0.5 Fructone 0.5 0.5 Irisantheme 2.0 2.0 Rhubafuran 0.5 0.5 Rosalva 0.8 0.8 Tetrahydro linalool 15.0 15.0 (E,Z)-9-undecenonitrile 1.0 0 Total 100 100

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  • 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)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Claims (19)

  1. Duftstoffzusammensetzung, umfassend eine Mischung von (9E)-Undecennitril, (9Z)-Undecennitril und 10-Undecennitril.
  2. Duftstoffzusammensetzung nach Anspruch 1, die einen zusätzlichen Duftstoffbestandteil umfasst.
  3. Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche, die einen zusätzlichen Bestandteil mit frischen hesperidischen Noten umfasst.
  4. Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche, die zusätzlich Bestandteile mit fruchtigen Akkorden umfasst.
  5. Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche, die zusätzlich Bestandteile mit Blütennoten umfasst.
  6. Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche, die zusätzlich Bestandteile mit grünen groben oder ländlichen oder agrestischen Noten umfasst.
  7. Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche, worin die Mischung von (9E)-Undecennitril, (9Z)-Undecennitril und 10-Undecennitril mindestens 30 Gew.-% an (9E)-Undecennitril umfasst.
  8. Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche, worin die Mischung von (9E)-Undecennitril, (9Z)-Undecennitril und 10-Undecennitril 40 bis 60 Gew.-% an (9E)-Undecennitril umfasst.
  9. Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche, wobei die Mischung von (9E)-Undecennitril, (9Z)-Undecennitril und 10-Undecennitril weniger als 40 Gew.-% an 10-Undecennitril umfasst.
  10. Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche, wobei die Mischung von (9E)-Undecennitril, (9Z)-Undecennitril und 10-Undecennitril 0.01 Gew.-% bis 30 Gew.-% an 10-Undecennitril umfasst.
  11. Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche, wobei die Mischung aus (9E)-Undecennitril, (9Z)-Undecennitril und 10-Undecennitril 5 Gew.-% bis 20 Gew.-% an 10-Undecennitril umfasst.
  12. Verbraucherprodukte, umfassend eine Duftstoffzusammensetzung nach einem der vorstehenden Ansprüche.
  13. Verbraucherprodukte nach Anspruch 12, umfassend eine Duftstoffzusammensetzung nach einem der Ansprüche 1 bis 11, wobei das Verbraucherprodukt eine aggressive, saure Charakteristik oder Eigenschaft aufweist.
  14. Verbraucherprodukte nach Anspruch 12, umfassend eine Duftstoffzusammensetzung nach einem der Ansprüche 1 bis 11, wobei das Verbraucherprodukt eine aggressive, oxidierende Eigenschaft aufweist.
  15. Verbraucherprodukte nach Anspruch 12, die eine Duftstoffzusammensetzung nach einem der Ansprüche 1 bis 11 umfassen, wobei das Verbraucherprodukt eine aggressive, alkalische Eigenschaft aufweist.
  16. Verbraucherprodukt, umfassend 0.01 bis 1 % einer Duftstoffzusammensetzung nach einem der Ansprüche 1 bis 11.
  17. Verwendung einer Duftstoffzusammensetzung nach einem der Ansprüche 1 bis 11 bei der Parfümerie.
  18. Verwendung einer Duftstoffzusammensetzung nach Anspruch 17 bei der funktionellen Parfümerie.
  19. Verfahren zur Herstellung parfümierter Verbraucherprodukte für die funktionelle Parfümerie durch Vermischung der Mischung von (9E)-Undecennitril, (9Z)-Undecennitril und 10-Undecennitril, die erhalten worden ist in einer Ein-Topf-Umsetzung, einem gegebenenfalls weiteren Duftsloffbestandteil, flüssigen und/oder festen Bestandteilen sowie einem Träger oder Medium.
EP20010116983 2000-07-21 2001-07-12 Eine Mischung von Nitrilen enthaltende Riechstoffzusammensetzung Expired - Lifetime EP1174117B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP20010116983 EP1174117B1 (de) 2000-07-21 2001-07-12 Eine Mischung von Nitrilen enthaltende Riechstoffzusammensetzung

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP00115699A EP1174116A1 (de) 2000-07-21 2000-07-21 Eine Mischung von Nitrilen enthaltende Riechstoffzusammensetzung
EP00115699 2000-07-21
EP20010116983 EP1174117B1 (de) 2000-07-21 2001-07-12 Eine Mischung von Nitrilen enthaltende Riechstoffzusammensetzung

Publications (2)

Publication Number Publication Date
EP1174117A1 EP1174117A1 (de) 2002-01-23
EP1174117B1 true EP1174117B1 (de) 2004-11-10

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3006685B1 (fr) * 2013-06-06 2016-07-22 Arkema France Procede d'hydroformylation et d'isomerisation controlees d'un nitril/ester/acide gras omega-insature.

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL136826C (de) * 1963-05-03
DE3932325A1 (de) * 1989-09-28 1991-04-11 Haarmann & Reimer Gmbh Alkadiennitrile, verfahren zu ihrer herstellung und ihre verwendung
DE19738576A1 (de) * 1997-09-04 1999-03-11 Basf Ag Verfahren zur Herstellung aliphatischer, ungesättigter Nitrile
US5888962A (en) * 1997-11-20 1999-03-30 Bush Boake Allen Inc. Nitrile perfumery material

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