EP0103125B1 - Aliphatic dicarboxylic acid esters as perfuming agents, and perfume compositions and perfumed products containing them - Google Patents

Aliphatic dicarboxylic acid esters as perfuming agents, and perfume compositions and perfumed products containing them Download PDF

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Publication number
EP0103125B1
EP0103125B1 EP83107355A EP83107355A EP0103125B1 EP 0103125 B1 EP0103125 B1 EP 0103125B1 EP 83107355 A EP83107355 A EP 83107355A EP 83107355 A EP83107355 A EP 83107355A EP 0103125 B1 EP0103125 B1 EP 0103125B1
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EP
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Prior art keywords
acid esters
weight
dicarboxylic acid
fragrances
aliphatic dicarboxylic
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Expired
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EP83107355A
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German (de)
French (fr)
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EP0103125A3 (en
EP0103125A2 (en
Inventor
Wolfgang Dr. Sturm
Gerd Mansfeld
Hans Reindl
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Haarmann and Reimer GmbH
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Haarmann and Reimer GmbH
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    • 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
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof

Definitions

  • the present invention relates to the use of aliphatic dicarboxylic acid esters as fragrance substances, fragrance substances containing certain mixtures of aliphatic dicarboxylic acid esters and perfume compositions and perfumed products which contain these fragrance substances.
  • the invention therefore relates to the use of the aliphatic dicarboxylic acid esters of the formula given as fragrances.
  • Preferred fragrances are mixtures of the dicarboxylic acid esters to be used according to the invention with lower alkanedicarboxylic acid esters.
  • Lower alkanedicarboxylic acid esters are essentially dimethyl or diisopropyl esters of decanedioic acid and nonanedioic acid.
  • the preferred fragrances may also contain traces (less than 2% by weight, based on the mixture as a whole) of shorter-chain alkanedicarboxylic acid esters.
  • Shorter-chain alkanedicarboxylic acid esters are, for example, the dimethyl or diisopropyl esters of hexanedioic acid (adipic acid), heptanedioic acid (pimelic acid) and octanedioic acid (suberic acid).
  • Fragrances are particularly preferred in which 1. a mixture of 30 to 50% by weight of dodecanedioic acid ester and 50 to 70% by weight of undecanedioic acid ester, 2. 0.5 to 10% by weight of decanedioic acid ester, 3. 0.5 to 5 wt .-% nonandioic acid ester and 4. traces of lower, dicarboxylic acid esters are included.
  • Dodecanedioic acid dimethyl ester nice after musk, hot aldehyde, after blown out candle, slightly woody.
  • Undecanedioic acid dilopropyl ester warm, powdery, woody.
  • fragrances according to the invention can be combined with other fragrances to form perfume compositions with expressive notes.
  • the aliphatic dicarboxylic acid esters according to the invention have an excellent fixing property and high stability and are therefore, inter alia, excellently suitable as fragrances for finished products in the cosmetics, fine perfumery, aerosol, detergent and in particular in the chemical-technical sector, for . B. for detergents., Hair care products, foam baths, bath salts, dishwashing detergents, machine dishwashing detergents, shampoos, fabric softeners, washing powder, soaps, antiperspirants, powders, creams, aftershave lotions, aftershave lotions, room air fresheners, toilet cleaners, room sprays, deodorant sprays, body sprays Insecticide sprays and sunscreens.
  • detergents Hair care products, foam baths, bath salts, dishwashing detergents, machine dishwashing detergents, shampoos, fabric softeners, washing powder, soaps, antiperspirants, powders, creams, aftershave lotions, aftershave lotions, room air fresheners, toilet cleaners, room sprays, deodor
  • the perfume composition became fuller in smell and much more harmonious.
  • the floral notes were reproduced more strongly and the wood notes became powdery and warmer.

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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)
  • Cosmetics (AREA)

Description

Die vorliegende Erfindung betrifft die Verwendung von aliphatischen Dicarbonsäureestern als Riechstoffe, Riechstoffe enthaltend bestimmte Gemische aliphatischer Dicarbonsäureester und Parfümkompositionen und parfümierte Produkte, die diese Riechstoffe enthalten.The present invention relates to the use of aliphatic dicarboxylic acid esters as fragrance substances, fragrance substances containing certain mixtures of aliphatic dicarboxylic acid esters and perfume compositions and perfumed products which contain these fragrance substances.

Es wurde gefunden, daß aliphatische Dicarbonsäureester der Formel

Figure imgb0001
in der

  • R eine Methyl- oder.Isopropylgruppe bedeutet und
  • n für die Zahl 9 oder 10 steht,

wertvolle Riechstoffe sind.It has been found that aliphatic dicarboxylic acid esters of the formula
Figure imgb0001
 in the
  • R represents a methyl or isopropyl group and
  • n represents the number 9 or 10,

are valuable fragrances.

Die Erfindung betrifft daher die Verwendung der aliphatischen Dicarbonsäureester der angegebenen Formel als Riechstoffe.The invention therefore relates to the use of the aliphatic dicarboxylic acid esters of the formula given as fragrances.

Die einzelnen Dicarbonsäureester sind zum Teil bekannt (C.A., Vol. 85 : 117 344 m ; DE-B-16 68 564) und können mit Hilfe bekannter Veresterungsverfahren aus den entsprechenden Säuren bzw. Säuregemischen hergestellt werden (Ullmanns Enzyklopädie der technischen Chemie, 4. Auflage, Bd. 11, 91-93).Some of the individual dicarboxylic acid esters are known (CA, Vol. 85: 117 344 m; DE-B-16 68 564) and can be prepared from the corresponding acids or acid mixtures using known esterification processes (Ullmann's Encyclopedia of Industrial Chemistry, 4. Edition, Vol. 11, 91-93).

Bevorzugte Riechstoffe sind Gemische der erfindungsgemäß zu verwendenden Dicarbonsäureester mit niedrigeren Alkandicarbonsäureestern. Niedrigere Alkandicarbonsäureester sind im wesentlichen Dimethyl- bzw. Diisopropylester der Decandisäure und der Nonandisäure. Gegebenenfalls enthalten die bevorzugten Riechstoffe noch Spuren (weniger als 2 Gew.-% bezogen auf das gesamte Gemisch) kürzerkettiger Alkandicarbonsäureester. Kürzerkettige Alkandicarbonsäureester sind beispielsweise die Dimethyl- bzw. Diisopropylester der Hexandisäure (Adipinsäure), Heptandisäure (Pimelinsäure) und Octandisäure (Korksäure).Preferred fragrances are mixtures of the dicarboxylic acid esters to be used according to the invention with lower alkanedicarboxylic acid esters. Lower alkanedicarboxylic acid esters are essentially dimethyl or diisopropyl esters of decanedioic acid and nonanedioic acid. The preferred fragrances may also contain traces (less than 2% by weight, based on the mixture as a whole) of shorter-chain alkanedicarboxylic acid esters. Shorter-chain alkanedicarboxylic acid esters are, for example, the dimethyl or diisopropyl esters of hexanedioic acid (adipic acid), heptanedioic acid (pimelic acid) and octanedioic acid (suberic acid).

Diese bevorzugten Riechstoffe kann man erhalten, wenn man das Dicarbonsäuregemisch, das bei der Herstellung von Dodecandisäure durch katalytische Oxidation von Cyclododecanol/Cyclododecanon anfällt (DAS 16 68 564) mit Methanol oder Isopropanol verestert.These preferred fragrances can be obtained by esterifying the dicarboxylic acid mixture obtained in the production of dodecanedioic acid by catalytic oxidation of cyclododecanol / cyclododecanone (DAS 16 68 564) with methanol or isopropanol.

Im besonderen bevorzugt werden Riechstoffe, in denen 1. ein Gemisch aus 30 bis 50 Gew.-% Dodecandisäureester und 50 bis 70 Gew.-% Undecandisäureester, 2. 0,5 bis 10 Gew.-% Decandisäureester, 3. 0,5 bis 5 Gew.-% Nonandisäureester sowie 4. Spuren niedrigerer, Dicarbonsäureester enthalten sind.Fragrances are particularly preferred in which 1. a mixture of 30 to 50% by weight of dodecanedioic acid ester and 50 to 70% by weight of undecanedioic acid ester, 2. 0.5 to 10% by weight of decanedioic acid ester, 3. 0.5 to 5 wt .-% nonandioic acid ester and 4. traces of lower, dicarboxylic acid esters are included.

Der Geruch der erfindungsgemäßen Riechstoffe läßt sich durch die folgende Geruchsbeschreibung wiedergeben:

  • Undecandisäuredimethylester: warm, holzig, pudrig, nach Karotte, Petersilie.
The smell of the fragrances according to the invention can be reproduced by the following description of the smell:
  • Undecandioic acid dimethyl ester: warm, woody, powdery, like carrot, parsley.

Dodecandisäuredimethylester: schön nach Moschus, heiß aldehydig, nach ·ausgebIasener Kerze, leicht holzig.Dodecanedioic acid dimethyl ester: nice after musk, hot aldehyde, after blown out candle, slightly woody.

Undecandisäuredilsopropylester: warm, pudrig, holzig.Undecanedioic acid dilopropyl ester: warm, powdery, woody.

Dodecandisäurediisopropylester: nach Moschus, warm, nach ausgeblaserner Kerze, schwach holzig.Dodecanedioic acid diisopropyl ester: after musk, warm, after blown out candle, slightly woody.

Die bevorzugten Riechstoffe zeichnen sich noch durch eine besonders im Nachgeruch ausgeprägte Note nach heißem Eisen und ausgeblasener Kerze aus, die sich besonders effektvoll mit anderen Noten, wie Aldehyd- und Bouquetnoten, kombinieren läßt.The preferred fragrances are characterized by a particularly pronounced aftertaste of hot iron and blown out candle, which can be combined particularly effectively with other notes, such as aldehyde and bouquet notes.

Die erfindungsgemäßen Riechstoffe können für sich allein oder in Mischungen miteinander oder in Kombination mit anderen an sich bekannten Riechstoffen (Arctander Parfume and Flavor Chemicals, Montclair, N.J. (USA), 1969) angewendet werden.The fragrances according to the invention can be used alone or in mixtures with one another or in combination with other fragrances known per se (Arctander Parfume and Flavor Chemicals, Montclair, N.J. (USA), 1969).

Die erfindungsgemäßen Riechstoffe lassen sich mit anderen Riechstoffen zu Parfümkompositionen mit ausdrucksstarken Noten kombinieren.The fragrances according to the invention can be combined with other fragrances to form perfume compositions with expressive notes.

Neben den hervorragenden Riechstoffeigenschaften weisen die erfindungsgemäßen aliphatischen Dicarbonsäureester eine ausgezeichnete fixierende Eigenschaft sowie eine hohe Stabilität auf und eignen sich deshalb unter anderem hervorragend als Riechstoffe für Fertigprodukte des Kosmetik-, Feinparfümerie-, Aerosol-, Waschmittel- und insbesondere des chemisch-technischen Sektors, z. B. für Detergenzien., Haarpflegemittel, Schaumbäder, Badesalz, Geschirrspülmittel, Maschinengeschirrspülmittel, Shampoos, Wäscheweichspülmittel, Waschpulver, Seifen, Antiperspirants, Puder, Cremes, Rasierwasser, Aftershave-Lotions, Raumluftverbesserer, WC-Reiniger, Raumsprays, Antiperspirantsprays, Deodorantsprays, Körpersprays, Insektizidsprays und Sonnenschutzmittel.In addition to the excellent fragrance properties, the aliphatic dicarboxylic acid esters according to the invention have an excellent fixing property and high stability and are therefore, inter alia, excellently suitable as fragrances for finished products in the cosmetics, fine perfumery, aerosol, detergent and in particular in the chemical-technical sector, for . B. for detergents., Hair care products, foam baths, bath salts, dishwashing detergents, machine dishwashing detergents, shampoos, fabric softeners, washing powder, soaps, antiperspirants, powders, creams, aftershave lotions, aftershave lotions, room air fresheners, toilet cleaners, room sprays, deodorant sprays, body sprays Insecticide sprays and sunscreens.

In diesen Präparaten werden die erfindungsgemäßen Riechstoffe im allgemeinen in einer Menge von 0,001 bis 10 Gew.-%, vorzugsweise von 0,01 bis 10 Gew: %, bezogen auf das fertige Präparat, eingesetzt.The odoriferous substances according to the invention are generally used in these preparations in an amount of 0.001 to 10% by weight, preferably 0.01 to 10% by weight, based on the finished preparation.

Die Herstellung dieser parfümierten Produkte erfolgt in üblicher Weise.These perfumed products are produced in the usual way.

Beispiel 1example 1 Herstellung eines Parfümöls :Production of a perfume oil:

Das Parfümöl wird nach der folgenden Rezeptur hergestellt (Zusammensetzung in Gewichtsteilen) :

Figure imgb0002
The perfume oil is produced according to the following recipe (composition in parts by weight):
Figure imgb0002

Beispiel 2Example 2

Zu dem nach Beispiel 1 hergestellten Parfümöl werden zu getrennten Proben jeweils 50 Gewichtsteile folgender Dicarbonsäureester gegeben :

  • a) Undecandisäuredimethylester,
  • b) Dodecandisäuredimethylester,
  • c) Undecandisäurediisopropylester,
  • d) Dodecandisäurediisopropyiester und
  • e) ein Gemisch aus 32 Gewichtsteilen Dodecandisäuredimethylester, 58 Gewichtsteilen Undecandisäuredimethylester, 8 Gewichtsteilen Decandisäuredimethylester und 2 Gewichtsteilen Nonandisäuredimethylester sowie Spuren niedrigerer Disäureestern.
50 parts by weight of the following dicarboxylic acid esters are added to the perfume oil produced according to Example 1:
  • a) undecanedioic acid dimethyl ester,
  • b) dimethyl dodecanedioate,
  • c) diisopropyl undecanedioate,
  • d) dodecanedioic acid diisopropyiester and
  • e) a mixture of 32 parts by weight of dodecanedioate, 58 parts by weight of undecanedioate, 8 parts by weight of decanedioate and 2 parts by weight of nonanedioate and traces of lower diacid esters.

Durch den Zusatz der Riechstoffe a) bis e) wurde die Parfümkomposition geruchlich voller und wesentlich harmonischer. Die Blumennoten wurden stärker wiedergegeben und die Holznoten wurden pudriger und wärmer. Außerdem erhielten die Kompositionen eine erhöhte Strahlung.By adding the fragrances a) to e), the perfume composition became fuller in smell and much more harmonious. The floral notes were reproduced more strongly and the wood notes became powdery and warmer. In addition, the compositions received increased radiation.

Claims (6)

1. Use of aliphatic dicarboxylic acid esters of the formula
Figure imgb0006
in which
R denotes a methyl or isopropyl group and
n represents the number 9 or 10,

as fragrances.
2. Fragances containing aliphatic dicarboxylic acid esters of the formula
Figure imgb0007
in which
R denotes a methyl or isopropyl group and
.n represents the number 9 or 10,

and 0.5 to 10 % by weight of decanedioic acid esters, 0.5 to 5 % by weight of nonanedioic acid esters and traces of alkanedioic acid esters having shorter chains.
3. Fragrances according to Claim 2, characterised in that they contain 1) a mixture of 30 to 50 % by weight of dodecanedioic acid esters and 50 to 70 % by weight of undecanedioic acid esters, 2) 0.5 to 10 % by weight of decanedioic acid esters, 3) 0.5 to 5 % by weight of nonanedioic acid esters and 4) traces of alkanedioic acid esters having shorter chains.
4. Perfume compositions and perfumed products containing a component consisting of fragrances of the formula
Figure imgb0008
in which
R denotes a methyl or isopropyl group and
n represents the number 9 or 10,

and, if appropriate, lower dicarboxylic acid esters.
5. Perfume compositions and perfumed products according to Claim 4, containing a component consisting of 1) a mixture of 30 to 50 % by weight of dodecanedioic acid esters and 50 to 70 % by weight of undecanedioic acid ester, 2) 0.5 to. 10 % by weight of decanedioic acid esters, 3) 0.5 to 5 % by weight of nonanedioic acid esters and 4) traces of alkanedioic acid esters having shorter chains.
6. Perfumed products containing 0.001 to 10 % by weight of the fragrances according to Claim 2 or 3, based on the finished product.
EP83107355A 1982-08-05 1983-07-27 Aliphatic dicarboxylic acid esters as perfuming agents, and perfume compositions and perfumed products containing them Expired EP0103125B1 (en)

Applications Claiming Priority (2)

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DE3229300 1982-08-05
DE19823229300 DE3229300A1 (en) 1982-08-05 1982-08-05 ALIPHATIC DICARBONIC ACID ESTERS AS FRAGRANCES AND PERFUME COMPOSITIONS CONTAINING THEM AND PERFUMED PRODUCTS

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EP0103125A2 EP0103125A2 (en) 1984-03-21
EP0103125A3 EP0103125A3 (en) 1986-01-29
EP0103125B1 true EP0103125B1 (en) 1987-10-21

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EP (1) EP0103125B1 (en)
JP (1) JPS5944309A (en)
DE (2) DE3229300A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3229300A1 (en) * 1982-08-05 1984-02-09 Haarmann & Reimer Gmbh, 3450 Holzminden ALIPHATIC DICARBONIC ACID ESTERS AS FRAGRANCES AND PERFUME COMPOSITIONS CONTAINING THEM AND PERFUMED PRODUCTS
US4568486A (en) * 1984-10-01 1986-02-04 International Flavors & Fragrances Inc. Augmenting or enhancing the leather aroma of perfume compositions, perfumed polymers, colognes and perfumed articles of the diethyl ester of 2-isopropyl-3-oxosuccinic acid
ES2331905T3 (en) * 1999-04-28 2010-01-20 Bellus Health (International) Limited COMPOSITIONS AND PROCEDURES TO TREAT AMYLOIDOSIS USING SULFANATE DERIVATIVES.
EP1707185A1 (en) * 2005-03-31 2006-10-04 International Flavors & Fragrances, Inc. Solvent materials and methods for preparing fragrance compositions
JP2017503789A (en) 2013-12-20 2017-02-02 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ New aromatic chemicals
CN111187166B (en) * 2020-01-17 2022-06-10 东莞波顿香料有限公司 Compound with tangerine peel fragrance, preparation method thereof and daily essence

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3576856A (en) * 1966-12-12 1971-04-27 Du Pont Process for simultaneous catalyst recovery and byproduct removal
JPS5294433A (en) * 1976-01-30 1977-08-09 Shiseido Co Ltd Perfume blender
IT1097281B (en) * 1978-06-26 1985-08-31 Brichima Spa PROCESS FOR THE PRODUCTION OF FUNCTIONAL ALIPHATIC ORGANIC COMPOUNDS
DE3229300A1 (en) * 1982-08-05 1984-02-09 Haarmann & Reimer Gmbh, 3450 Holzminden ALIPHATIC DICARBONIC ACID ESTERS AS FRAGRANCES AND PERFUME COMPOSITIONS CONTAINING THEM AND PERFUMED PRODUCTS

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JPS5944309A (en) 1984-03-12
DE3229300A1 (en) 1984-02-09
EP0103125A3 (en) 1986-01-29
US4528124A (en) 1985-07-09
DE3374136D1 (en) 1987-11-26
EP0103125A2 (en) 1984-03-21

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