EP0103125A2 - 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
EP0103125A2
EP0103125A2 EP83107355A EP83107355A EP0103125A2 EP 0103125 A2 EP0103125 A2 EP 0103125A2 EP 83107355 A EP83107355 A EP 83107355A EP 83107355 A EP83107355 A EP 83107355A EP 0103125 A2 EP0103125 A2 EP 0103125A2
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Prior art keywords
acid esters
dicarboxylic acid
fragrances
weight
esters
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EP83107355A
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German (de)
French (fr)
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EP0103125B1 (en
EP0103125A3 (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 fragrances and their use in perfume compositions and perfumed products.
  • Some of the individual dicarboxylic acid esters are known (CA, Vol. 85: 117 344 m; DE-AS 16 68 564) and can be produced from the corresponding acids or acid mixtures using known esterification processes (Ullmanns Encyclopedia of Industrial Chemistry, 4th edition, Vol. 11, 91-93).
  • Preferred fragrances are mixtures of the dicarboxylic acid esters according to the invention with lower dicarboxylic acid esters.
  • Lower dicarboxylic 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 dicarboxylic acid esters.
  • Shorter-chain dicarboxylic 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 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.
  • Fragrances in which 30 to 50% by weight of dodecanedioic acid ester, 50 to 70% by weight of undecanedioic acid ester, 0.5 to 10% by weight of decanedioic acid ester and 0.5 to 5% by weight of nonanedioic acid ester and traces are lower are particularly preferred Dicarboxylic acid esters are included.
  • 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.
  • 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 perfumee and Flavor Chemicals, Montclair, N.J. (USA), 1969).
  • fragrances according to the invention can be combined with other fragrances to give 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 suitable, inter alia Excellent as fragrances for finished products in the cosmetics, fine perfumery, aerosol, detergents and especially in the chemical-technical sector, e.g. for detergents, hair care products, bubble baths, bath salts, dishwashing detergents, machine dishwashing detergents, shampoos, fabric softening detergents, washing powder, soaps, antiperspirants, powder , Creams, aftershave lotions, aftershave lotions, room air improvers, toilet cleaners, room sprays, antiperspirant sprays, deodorant sprays, body sprays, insecticide sprays and sunscreens.
  • the fragrance 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.
  • 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)

Abstract

Aliphatische Dicarbonsäureester der Formel R-O-?-(CH2)n-?-OR in der R eine Methyl- oder Isopropylgruppe bedeutet und n für die Zahl 9 oder 10 steht, werden als Riechstoffe verwendet. Sie können als Komponenten in Parfümkompositionen und parfümierten Produkten eingesetzt werden.Aliphatic dicarboxylic acid esters of the formula R-O -? - (CH2) n -? - OR in which R represents a methyl or isopropyl group and n represents the number 9 or 10 are used as fragrances. They can be used as components in perfume compositions and perfumed products.

Description

Die vorliegende Erfindung betrifft die Verwendung von aliphatischen Dicarbonsäureestern als Riechstoffe und ihre Anwendung in Parfümkompositionen und parfümierten Produkten.The present invention relates to the use of aliphatic dicarboxylic acid esters as fragrances and their use in perfume compositions and perfumed products.

Es wurden Riechstoffe, die aliphatische Dicarbonsäuren der Formel

Figure imgb0001
in der

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

und gegebenenfalls niedrigere Dicarbonsäureester enthalten, gefunden.There were fragrances, the aliphatic dicarboxylic acids of the formula
Figure imgb0001
 in the
  • R represents a methyl or isopropyl group and
  • n represents the number 9 or 10,

and optionally contain lower dicarboxylic acid esters.

Die einzelnen Dicarbonsäureester sind zum Teil bekannt (C.A., Vol. 85: 117 344 m; DE-AS 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-AS 16 68 564) and can can be produced from the corresponding acids or acid mixtures using known esterification processes (Ullmanns Encyclopedia of Industrial Chemistry, 4th edition, Vol. 11, 91-93).

Bevorzugte Riechstoffe sind Gemische der erfindungsgemäßen Dicarbonsäureester mit niedrigeren Dicarbonsäureestern. Niedrigere Dicarbonsäureester 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 Dicarbonsäureester. Kürzerkettige Dicarbonsäureester sind beispielsweise die Dimethyl- bzw. Diisopropylester der Hexandisäure (Adipinsäure), Heptandisäure (Pimelinsäure) und Octandisäure (Korksäure).Preferred fragrances are mixtures of the dicarboxylic acid esters according to the invention with lower dicarboxylic acid esters. Lower dicarboxylic 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 dicarboxylic acid esters. Shorter-chain dicarboxylic 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 30 bis 50 Gew.-% Dodecandisäureester, 50 bis 70 Gew.-% Undecandisäureester, 0,5 bis 10 Gew.-% Decandisäureester und 0,5 bis 5 Gew.-% Nonandisäureester sowie Spuren niedrigerer Dicarbonsäureester enthalten sind.Fragrances in which 30 to 50% by weight of dodecanedioic acid ester, 50 to 70% by weight of undecanedioic acid ester, 0.5 to 10% by weight of decanedioic acid ester and 0.5 to 5% by weight of nonanedioic acid ester and traces are lower are particularly preferred Dicarboxylic acid esters are included.

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

  • Undecandisäuredimethylester:
    • warm, holzig, pudrig, nach Karotte, Petersilie. Dodecandisäuredimethylester:
    • schön nach Moschus, heiß aldehydig, nach ausgeblasener Kerze, leicht holzig.
  • Undecandisäurediisopropylester:
    • warm, pudrig, holzig.
  • Dodecandisäurediisopropylester:
    • nach Moschus, warm, nach ausgeblaserner Kerze, schwach holzig.
The smell of the fragrances according to the invention can be reproduced by the following description of the smell:
  • Undecanedioic acid dimethyl ester:
    • warm, woody, powdery, like carrot, parsley. Dodecanedioic acid dimethyl ester:
    • nice like musk, hot aldehyde, after blown out candle, slightly woody.
  • Undecanedioic acid diisopropyl ester:
    • warm, powdery, woody.
  • Diisopropyl dodecanedioate:
    • like 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 give 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 suitable, inter alia Excellent as fragrances for finished products in the cosmetics, fine perfumery, aerosol, detergents and especially in the chemical-technical sector, e.g. for detergents, hair care products, bubble baths, bath salts, dishwashing detergents, machine dishwashing detergents, shampoos, fabric softening detergents, washing powder, soaps, antiperspirants, powder , Creams, aftershave lotions, aftershave lotions, room air improvers, toilet cleaners, room sprays, antiperspirant 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 fragrance 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):

  • 20 Styrolylacetat,
  • 50 Iraldein,
  • 100 Phenylethylalkohol,
  • 72 p-tert.-Butylcyclohexylacetat,
  • 50 Zimtalkohol,
  • 30 Patschuliöl,
  • 3 Galbanum Resin,
  • 70 4-(4-Hydroxy-4-methyl-pentyl)-3-cyclohexen-1-carboxaldehyd,
  • 50 α-Hexylzimtaldehyd,
  • 5 Undecylenaldehyd,
  • 30 Benzylacetat,
  • 20 Dimethylbenzylcarbinolacetat,
  • 50 Abietinsäuremethylester.
The perfume oil is produced according to the following recipe (composition in parts by weight):
  • 20 styrolylacetate,
  • 50 Iraldein,
  • 100 phenylethyl alcohol,
  • 72 p-tert-butylcyclohexyl acetate,
  • 50 cinnamon alcohol,
  • 30 patchouli oil,
  • 3 galbanum resin,
  • 70 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde,
  • 50 α-hexyl cinnamaldehyde,
  • 5 undecylenaldehyde,
  • 30 benzyl acetate,
  • 20 dimethylbenzylcarbinol acetate,
  • 50 methyl abietic esters.

Beisniel 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) Dodecandisäurediisopropylester 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) diisopropyl dodecanedioate 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 (7)

1. Riechstoffe, enthaltend aliphatische Dicarbonsäureester der Formel
Figure imgb0002
in der R eine Methyl- oder Isopropylgruppe bedeutet und n für die Zahl 9 oder 10 steht,
und gegebenenfalls niedrigere Dicarbonsäureester.1. Fragrances containing aliphatic dicarboxylic acid esters of the formula
Figure imgb0002
 in the R represents a methyl or isopropyl group and n represents the number 9 or 10,
and optionally lower dicarboxylic acid esters. 2. Riechstoffe nach Anspruch 1, dadurch gekennzeichnet, daß der Riechstoff als niedrigere Dicarbonsäureester 0,5 bis 10 Gewichtsteile Decandisäureester, 0,5 bis 5 Gew.-% Nonandisäureester und Spuren von kürzerkettigen Disäureestern enthält.2. Fragrances according to claim 1, characterized in that the fragrance contains 0.5 to 10 parts by weight of decanedioic acid ester, 0.5 to 5% by weight of nonanedioic acid ester and traces of shorter-chain diacid esters as lower dicarboxylic acid esters. 3. Riechstoffe nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß sie 30 bis 50 Gew.-% Dodecandisäureester, 50 bis 70 Gew.-% Undecandisäureester, 0,5 bis 10 Gew.-% Decandisäureester, 0,5 bis 5 Gew.-% Nonandisäureester sowie Spuren kürzerkettigerer Disäureester enthalten.3. Fragrances according to claims 1 to 3, characterized in that they contain 30 to 50% by weight of dodecanedioic acid ester, 50 to 70% by weight of undecanedioic acid ester, 0.5 to 10% by weight of decanedioic acid ester, 0.5 to 5% by weight .-% contain nonandioic acid esters and traces of shorter-chain diacid esters. 4. Verwendung von aliphatischen Dicarbonsäureestern der Formel
Figure imgb0003
in der R eine Methyl- oder Isopropylgruppe bedeutet und n für die Zahl 9 oder 10 steht,
als Riechstoffe.4. Use of aliphatic dicarboxylic acid esters of the formula
Figure imgb0003
 in the R represents a methyl or isopropyl group and n represents the number 9 or 10,
as fragrances. 5. Parfümkompositionen und parfümierte Produkte, enthaltend eine Komponente bestehend aus Riechstoffen der Formel
Figure imgb0004
in der R eine Methyl- oder Isopropylgrupe bedeutet und n für die Zahl 9 oder 10 steht,
und gegebenenfalls niedrigere Dicarbonsäureester.5. Perfume compositions and perfumed products containing a component consisting of fragrances of the formula
Figure imgb0004
 in the R represents a methyl or isopropyl group and n represents the number 9 or 10,
and optionally lower dicarboxylic acid esters. 6. Parfümkompositionen und parfümierte Produkte nach Anspruch 5, enthaltend eine Komponente bestehend aus 30 bis 50 Gew.-% Dodecandisäureester, 50 bis 70 Gew.-% Undecandisäureester, 0,5 bis 10 Gew.-% Decandisäureester, 0,5 bis 5 Gew.-% Nonandisäureester sowie Spuren niedrigerer Disäureester.6. Perfume compositions and perfumed products according to claim 5, containing a component consisting of 30 to 50 wt .-% dodecanedioate, 50 to 70 wt .-% undecanedioate, 0.5 to 10 wt .-% decanedioate, 0.5 to 5 wt .-% nonandioic acid esters and traces of lower diacid esters. 7. Parfümierte Produkte, enthaltend 0,001 bis 10 Gew.-% der Riechstoffe nach den Ansprüchen 1 bis 3, bezogen auf das fertige Präparat.7. Perfumed products containing 0.001 to 10 wt .-% of the fragrances according to claims 1 to 3, based on the finished preparation.
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)

Application Number Priority Date Filing Date Title
DE19823229300 DE3229300A1 (en) 1982-08-05 1982-08-05 ALIPHATIC DICARBONIC ACID ESTERS AS FRAGRANCES AND PERFUME COMPOSITIONS CONTAINING THEM AND PERFUMED PRODUCTS
DE3229300 1982-08-05

Publications (3)

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

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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015091924A1 (en) * 2013-12-20 2015-06-25 Basf Se Novel aroma chemicals
CN111187166A (en) * 2020-01-17 2020-05-22 东莞波顿香料有限公司 Compound with tangerine peel fragrance, preparation method thereof and daily essence

Families Citing this family (4)

* 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
CA2369997C (en) * 1999-04-28 2009-11-17 Queen's University At Kingston Compositions and methods for treating amyloidosis
EP1707185A1 (en) * 2005-03-31 2006-10-04 International Flavors & Fragrances, Inc. Solvent materials and methods for preparing fragrance compositions

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2339396A1 (en) * 1976-01-30 1977-08-26 Shiseido Co Ltd PROCESS FOR IMPROVING THE QUALITY OF PERFUME PERFUMES
FR2429768A1 (en) * 1978-06-26 1980-01-25 Brichima Spa PROCESS FOR THE PRODUCTION OF BIFUNCTIONAL ALIPHATIC ORGANIC COMPOUNDS

Family Cites Families (2)

* 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
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2339396A1 (en) * 1976-01-30 1977-08-26 Shiseido Co Ltd PROCESS FOR IMPROVING THE QUALITY OF PERFUME PERFUMES
FR2429768A1 (en) * 1978-06-26 1980-01-25 Brichima Spa PROCESS FOR THE PRODUCTION OF BIFUNCTIONAL ALIPHATIC ORGANIC COMPOUNDS

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015091924A1 (en) * 2013-12-20 2015-06-25 Basf Se Novel aroma chemicals
US10066188B2 (en) 2013-12-20 2018-09-04 Basf Se Aroma chemicals
CN111187166A (en) * 2020-01-17 2020-05-22 东莞波顿香料有限公司 Compound with tangerine peel fragrance, preparation method thereof and daily essence
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

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US4528124A (en) 1985-07-09
EP0103125B1 (en) 1987-10-21
DE3229300A1 (en) 1984-02-09
DE3374136D1 (en) 1987-11-26
EP0103125A3 (en) 1986-01-29
JPS5944309A (en) 1984-03-12

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