EP0586442B1 - Utilisation de derives isomeres 1,1,1-trialkyl-2-phenyl-ethane comme parfums, et compositions de parfums renfermant ces derives - Google Patents

Utilisation de derives isomeres 1,1,1-trialkyl-2-phenyl-ethane comme parfums, et compositions de parfums renfermant ces derives Download PDF

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Publication number
EP0586442B1
EP0586442B1 EP92910449A EP92910449A EP0586442B1 EP 0586442 B1 EP0586442 B1 EP 0586442B1 EP 92910449 A EP92910449 A EP 92910449A EP 92910449 A EP92910449 A EP 92910449A EP 0586442 B1 EP0586442 B1 EP 0586442B1
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EP
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Prior art keywords
trialkyl
fragrances
isomeric
ppm
substances
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EP92910449A
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German (de)
English (en)
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EP0586442A1 (fr
Inventor
Klaus Bruns
Michael Dischmann
Thomas Markert
Heiner Westermann
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • the invention relates to the use of isomeric 1,1,1-trialkyl-2-phenyl-ethane derivatives as fragrances.
  • fragrance industry has a constant need for new fragrances with interesting fragrances to complement the range of naturally available fragrances and to make the necessary adjustments to changing fashionable tastes, as well as the ever-increasing need for odor improvers for everyday products such as To be able to cover cosmetics and cleaning agents.
  • Acetic acid (1-phenyl-2,2,2-trichloroethyl) ester is a well-known, commercially available fragrance which has a mild floral-rosy smell.
  • halogenated compounds are increasingly viewed critically by the consumer, so that there is a need for suitable substitutes.
  • the C atom directly adjacent to the phenyl radical in the compounds of the general formula (I) represents a center of chirality, so that these compounds can exist in various spatial forms.
  • the compounds according to the invention are obtained as mixtures of the corresponding isomers and as such are used as a fragrance used. If desired, however, the enantiomerically pure compounds can also be used alone as a fragrance.
  • the products to be used as fragrances according to the invention are produced by methods known per se in preparative organic chemistry.
  • pivalinaldehyde can be converted to 2,2-dimethyl-1-phenyl-propanol (II) by Grignard reaction with phenylmagnesium bromide, which can be converted, for example, by reaction with acetic anhydride in pyridine or dimethylaminopyridine to acetate (Ia), with dimethyl carbonate to carbonate ( Ib) or with ethyl vinyl ether in the presence of an acidic catalyst to form the acetal (Ic).
  • Preference is given to using those compounds of the general formula (I) as odoriferous substances in which the radicals R1 to R3 are methyl groups, in particular those in which the radical R4 is also an acyl radical having 1 to 3 carbon atoms.
  • acetic acid (2,2-dimethyl-1-phenyl-propyl) ester (Ia) is particularly preferred.
  • Compound (Ia) in particular has remarkable odor properties that are very much in demand in perfumery, namely rosy-woody with complex shades and great charisma.
  • This particular olfactory characteristic of the rose type. is original and new and deviates significantly from the olfactory characteristics of the acetic acid (1-phenyl-2,2,2-trichloroethyl) ester known as a fragrance, which is particularly surprising.
  • the compound (Ia) enhances the harmony and charisma as well as the adhesion, whereby the dosage can be adjusted to the desired fragrance note, taking into account the other components of the composition.
  • the compounds of the formula (I) are particularly suitable for modifying and enhancing known compositions.
  • their extraordinary olfactory strength should be emphasized, which generally contributes to the refinement of the composition.
  • the usable proportions of the compounds according to the invention or their mixtures in fragrance compositions range from 1 to 70 percent by weight, based on the mixture as a whole.
  • Mixtures of the compounds (I) according to the invention and compositions of this type can be used for perfuming cosmetic preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, toothpastes, mouthwashes, deodorants as well as in alcoholic perfumery (e.g. Eau de Cologne, Eau de toilet, tincts) can be used.
  • perfuming technical products such as detergents and cleaning agents, fabric softeners and textile treatment agents or tobacco.
  • compositions are added to them in an olfactory effective amount, in particular in a concentration of 0.05 to 2 percent by weight, based on the entire product.
  • these values are not intended to represent any limit values, since the experienced perfumer can achieve effects with even lower concentrations or build new types of complexes with even higher doses.
  • the compounds of the general formula I were prepared starting from 2,2-dimethyl-1-phenyl-propanol II, which was obtained as follows: 235.5 g (1.5 mol) of bromobenzene were added dropwise to 36.5 g (1.5 mol) of magnesium shavings in 300 ml of ether, the reaction mixture was diluted with a further 400 ml of ether and stirred under reflux for 30 minutes. After a solution of 103.3 g (1.2 mol) of pivalaldehyde in 130 ml of ether was added dropwise, the mixture was stirred under reflux for a further 2 hours and hydrolyzed with ice / ammonium chloride solution.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne l'utilisation, comme parfums, de dérivés isomères 1,1,1-trialkyl-2-phényl-éthane de formule générale (I), dans laquelle les restes R1 à R3 désignent, indépendamment les uns des autres, des groupes alkyle de 1 à 3 atomes de carbone, le reste R4 est un hydrogène ou un groupe alkyle, un groupe acyle, un groupe alkoxycarbonyle ou un groupe alkoxyalkyle ayant au total de 2 à 5 atomes de carbone. Ces composés, notamment le (2,2-diméthyl-1-phényl-propyl)-ester de l'acide acétique, ont la particularité de présenter un profil odorant boisé-rosé de nature complexe et d'une grande exhalaison et peuvent être mélangés entre eux ou avec d'autres parfums dans les proportions les plus diverses pour donner de nouvelles compositions de parfums, généralement dans une proportion de 1 à 70 % en poids, par rapport à la composition totale. Ces compositions peuvent être utilisées pour parfumer des préparations cosmétiques et des produits industriels, ainsi qu'en parfumerie alcoolisée.

Claims (6)

  1. Utilisation de dérivés de 1,1,1-trialcoyl-2-phényl-éthane isomères de formule générale (I)
    Figure imgb0007
     dans laquelle :
    les restes R¹ à R³ indépendamment les uns des autres, signifient des groupes alcoyle ayant de 1 à 3 atomes de carbone,
    le reste R⁴ signifie un groupe alcoyle ou acyle ayant de 1 à 5 atomes de carbone, ou un groupe alcoxycarbonyle ou un groupe alcoxyalcoyle ayant de 2 à 5 atomes de carbone code substances odorantes.
  2. Utilisation de dérivés de 1,1,1-trialcoyL-2-phényl-éthane isomères selon la revendication 1 dans laquelle les restes R¹ à R³ signifient des groupes méthyle, code substances odorantes.
  3. Utilisation de dérivés de 1,1,1-trialcoyl-2-phényl-éthane isomères selon la revendication 2, dans laquelle R⁴ représente un reste acyle ayant de 1 à 3 atomes de C, comme substances odorantes.
  4. Utilisation de dérivés de 1,1,1-trialcoyl-2-phényléthane isomères selon la revendication 3, dans laquelle R⁴ représente un groupe acétyle, comme substances odorantes.
  5. Compositions de substances odorantes, caractérisées par une teneur en un dérivé de 2,2-dialcoyl-1-phényl-propane de formule I selon la revendication 1 à 4 en une quantité allant de 1 à 70 % en poids, rapportée à la composition totale.
  6. Utilisation de mélanges de dérivés de 1,1,1-trialcoyl-2-phényl-éthane de formule I selon les revendications 1 à 4, conjointement avec des composants de substances odorantes naturelles et synthétiques connus comme substances odorantes dans des préparations cosmétiques, des produits industriels ou dans la parfumerie alcoolisée.
EP92910449A 1991-05-29 1992-05-20 Utilisation de derives isomeres 1,1,1-trialkyl-2-phenyl-ethane comme parfums, et compositions de parfums renfermant ces derives Expired - Lifetime EP0586442B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4117669 1991-05-29
DE19914117669 DE4117669A1 (de) 1991-05-29 1991-05-29 Verwendung isomerer 1,1,1-trialkyl-2-phenyl-ethan-derivate als riechstoffe, sowie diese enthaltende riechstoffkompositionen
PCT/EP1992/001118 WO1992021738A1 (fr) 1991-05-29 1992-05-20 Utilisation de derives isomeres 1,1,1-trialkyl-2-phenyl-ethane comme parfums, et compositions de parfums renfermant ces derives

Publications (2)

Publication Number Publication Date
EP0586442A1 EP0586442A1 (fr) 1994-03-16
EP0586442B1 true EP0586442B1 (fr) 1995-01-04

Family

ID=6432762

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EP92910449A Expired - Lifetime EP0586442B1 (fr) 1991-05-29 1992-05-20 Utilisation de derives isomeres 1,1,1-trialkyl-2-phenyl-ethane comme parfums, et compositions de parfums renfermant ces derives

Country Status (4)

Country Link
EP (1) EP0586442B1 (fr)
JP (1) JPH06507659A (fr)
DE (2) DE4117669A1 (fr)
WO (1) WO1992021738A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008285422A (ja) * 2007-05-15 2008-11-27 Maruzen Pharmaceut Co Ltd Ｄｎａ損傷抑制剤及びグルタチオン産生促進剤

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1293747B (de) * 1965-08-27 1969-04-30 Universal Oil Prod Co Verfahren zur Herstellung von Allyl-ª‰-phenylpropionaten
US4490284A (en) * 1982-09-29 1984-12-25 Dragoco Gerberding & Co. Gmbh 1,1-Di(C1 -C6 -alkyl)-2-phenyl-ethane derivatives as perfuming ingredients

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
S.ARCTANDER 'Perfume and flavor chemicals' 1969 , S.ARCTANDER , MONTCLAIR,N.J.,U.S.A., S. 1044 *

Also Published As

Publication number Publication date
EP0586442A1 (fr) 1994-03-16
DE4117669A1 (de) 1992-12-03
DE59201157D1 (de) 1995-02-16
WO1992021738A1 (fr) 1992-12-10
JPH06507659A (ja) 1994-09-01

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