EP0905222A2 - Moschus-Riechstoffe - Google Patents
Moschus-Riechstoffe Download PDFInfo
- Publication number
- EP0905222A2 EP0905222A2 EP98117335A EP98117335A EP0905222A2 EP 0905222 A2 EP0905222 A2 EP 0905222A2 EP 98117335 A EP98117335 A EP 98117335A EP 98117335 A EP98117335 A EP 98117335A EP 0905222 A2 EP0905222 A2 EP 0905222A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- ethylene
- mixtures
- mixture
- perfume
- musk
- 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.)
- Withdrawn
Links
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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0084—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing more than six atoms
Definitions
- the present invention relates to mixtures of ethylene dodecanedioate and ethylene undecanedioate, containing such mixtures as fragrance components Perfume oils and products perfumed with such perfume oils.
- a relatively inexpensive one in the group of macrocyclic musk fragrances Compound is the cyclic ethylene glycol ester of dodecanedicarboxylic acid (Ethylene dodecanedioate, e.g. commercially available as Arova N from Huls).
- this compound is not suitable substitute for polycyclic aromatic musk fragrances.
- the addition of the lower homologue, of the cyclic ethylene glycol ester of undecanedicarboxylic acid (Ethylene undecanedioate) causes an olfactory effect which makes it noticeable that the resulting mixture is much better the type of smell of polycyclic aromatic musk fragrances.
- the invention thus relates to mixtures comprising a) ethylene dodecanedioate and b) ethylene undecanedioate, the amount b) being 5 to 60, preferably 30 to 50 % By weight, based on the sum (a + b), is.
- Mixtures with such compositions also have the advantage that that they are very inexpensive to manufacture.
- Mixtures of dodecanoic and undecanedicarboxylic acids fall as cheap by-products in the oxidation of cyclododecene to dodecanedicarboxylic acid (precursor for polyamide-1,12). It means that Mixtures of ethylene dodecanedioate and ethylene undecanedioate are inexpensive Represent an alternative to polycyclic aromatic musk fragrances.
- the preparation of the mixtures of ethylene dodecanedioate and ethylene undecanedioate can in a manner known per se by esterification of the corresponding dicarboxylic acid mixture with ethylene glycol and subsequent thermal depolymerization the resulting polyester blend, e.g. in analogy to that in the German patent specification 25 47 267 given regulations.
- the production of the Polyester can by heating the dicarboxylic acid mixture with ethylene glycol take place, generally at 130 to 200 ° C, preferably at 150 to 170 ° C.
- the depolymerization can be carried out thermally with heavy metal catalysis, in general between 200 and 300 ° C, preferably between 260 and 270 ° C.
- Catalysts are preferably suitable for tin compounds, e.g. Dibutyltin oxide, dibutyltin dilaurate and dibutyltin bis-2-ethylhexanoate.
- the Reaction can be carried out without using a solvent, but is also possible in the presence of a solvent.
- the mixtures according to the invention are suitable because of their typical organoleptic Properties excellent for use in perfume compositions and here especially as a replacement for polycyclic aromatic Musk compounds. They can also be mixed in very well with other fragrances different, different proportions to new perfume compositions combine. In such perfume compositions the amount is the mixtures according to the invention generally 1 to 40, preferably 5 to 20 % By weight, based on the entire composition.
- perfume compositions can be used as fine perfumes not only in alcoholic solutions used, but also for perfuming cosmetics, e.g. Creams, lotions, aerosols, toilet soaps, etc., household products such as cleaning and washing agents, fabric softeners, disinfectants, textile treatment agents and other technical products are used, the amount of perfume composition 0.1 to 40, preferably 0.5 to 20 wt .-%, based on the perfumed Product.
- perfuming cosmetics e.g. Creams, lotions, aerosols, toilet soaps, etc.
- household products such as cleaning and washing agents, fabric softeners, disinfectants, textile treatment agents and other technical products are used, the amount of perfume composition 0.1 to 40, preferably 0.5 to 20 wt .-%, based on the perfumed Product.
- 105 g of a technical mixture of 40 to 60% dodecundic acid, 30 to 50% Undecanedioic acid, 3 to 8% decanedioic acid and 0 to 4% nonanedioic acid are used 105 g of ethylene glycol are added and the mixture is slowly heated to 150 ° C; at about 130 to 140 ° C starts the elimination of water. After the end of the dehydration, the removal excess ethylene glycol increases the temperature to 170 ° C and the Reaction apparatus slowly evacuated to a pressure of 1 mbar. The one behind resulting dicarboxylic acid / ethylene glycol polyester with 1.5 g of dibutyltin oxide mixed and slowly melted in a preheated to 270 ° C.
- Depolymerization apparatus metered with a wall-mounted stirrer. At a The monomeric cleavage products slowly distill off under a pressure of 0.1 mbar. After Washing and activated carbon treatment are a total of about 150g of a mixture get that a pleasant, multi-faceted musk smell with a slight has a floral, greasy undertone. According to gas chromatographic analysis this mixture roughly contains the composition of the starting material between 40 and 60% ethylene dodecanedioate, 30 to 50% ethylene undecanedioate, 3 to 8% ethylene decanedioate and 0 to 4% ethylene nonanedioate.
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)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
- A =
- CH2; O; O-CH2-CH2-O-CO;
- A =
- CH2; O; CH = CH;
- x + y =
- 8 bis 15
Styrolylacetat | 2 |
Dihydromyrcenol | 3 |
Citronenöl | 15 |
Aldehyd C14 sog. | 18 |
Linalool | 20 |
Phenylethylalkohol | 10 |
Citronellol | 10 |
Benzylacetat | 10 |
Methyldihydrojasmonat | 50 |
Hexylzimtaldehyd | 50 |
Jasminöl synthetisch | 20 |
Ylang-Ylang-Öl synthetisch | 10 |
Isomethylionon gamma | 50 |
Eugenol | 2 |
Isoeugenol | 1 |
Vanillin | 2 |
Cumarin | 10 |
Oryclon H & R | 30 |
Patchoulyöl farblos | 2 |
Sandel H & R | 50 |
Bergamotteöl synthetisch | 100 |
Diethylphthalat | 335 |
Dipropylenglycol | 100 |
- die Testmischungen a und d geruchlich am ähnlichsten sind,
- Testmischung d harmonischer und voluminöser riecht als die Testmischungen b und c,
- die blumige Herznote (Bouquet) in Testmischung d im Vergleich zu b und c deutlich verstärkt wird und
- Testmischung d im Vergleich zu b und c einen wesentlich facettenreicheren Dufteindruck bewirkt.
Claims (4)
- Mischungen enthaltend a) Ethylendodecandioat und b) Ethylenundecandioat, wobei die Menge b) 5 bis 60 Gew.-%, bezogen auf die Summe (a + b), beträgt.
- Mischungen nach Ansprch 1, wonach die Menge b) 30 bis 50 Gew.-%, bezogen auf die Summe (a + b), beträgt.
- Parfumöle mit einem Gehalt einer Mischung nach Anspruch 1.
- Mit Parfumölen nach Anspruch 3 parfumierte Produkte.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19742307A DE19742307A1 (de) | 1997-09-25 | 1997-09-25 | Neue Moschus-Riechstoffe |
DE19742307 | 1997-09-25 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0905222A2 true EP0905222A2 (de) | 1999-03-31 |
EP0905222A3 EP0905222A3 (de) | 2000-04-12 |
Family
ID=7843580
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98117335A Withdrawn EP0905222A3 (de) | 1997-09-25 | 1998-09-12 | Moschus-Riechstoffe |
Country Status (7)
Country | Link |
---|---|
US (1) | US6034052A (de) |
EP (1) | EP0905222A3 (de) |
JP (1) | JPH11209783A (de) |
AU (1) | AU729020B2 (de) |
BR (1) | BR9803591A (de) |
CA (1) | CA2248403A1 (de) |
DE (1) | DE19742307A1 (de) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10041198B4 (de) | 2000-08-23 | 2004-01-15 | Symrise Gmbh & Co. Kg | Verfahren zur Herstellung makrocyclischer Ester |
US20070032401A1 (en) * | 2003-03-13 | 2007-02-08 | Flexitral, Inc. | Macrocyclic musks |
CA2956623C (en) | 2014-07-30 | 2020-10-27 | Georgia-Pacific Consumer Products Lp | Air freshener dispensers, cartridges therefor, systems, and methods |
US20160376524A1 (en) * | 2015-06-29 | 2016-12-29 | Takasago International Corporation (Usa) | Musk compositions and methods of use thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2328704A1 (fr) * | 1975-10-22 | 1977-05-20 | Huels Chemische Werke Ag | Procede de preparation de diesters cycliques de l'acide dodecane-dioique |
US4251448A (en) * | 1979-07-24 | 1981-02-17 | Bayer Aktiengesellschaft | Macrocyclic diesters |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4157330A (en) * | 1975-10-22 | 1979-06-05 | Chemische Werke Huels Aktiengesellschaft | Process for the production of cyclic diesters of dodecanedioic acid |
US4218379A (en) * | 1977-09-21 | 1980-08-19 | Emery Industries, Inc. | Process for the production of macrocyclic esters |
US4165321A (en) * | 1977-09-21 | 1979-08-21 | Harris Eugene G | Process for the production of heterocyclic compounds |
US4331603A (en) * | 1979-05-25 | 1982-05-25 | Emery Industries, Inc. | Process for improving the fragrance properties of macrocyclic compounds obtained by thermal depolymerization |
US4393223A (en) * | 1979-09-10 | 1983-07-12 | Emery Industries, Inc. | Process for the production of macrocyclic esters and lactones utilizing mixed metal catalysts |
US4499288A (en) * | 1981-07-22 | 1985-02-12 | National Distillers And Chemical Corporation | Process for the production of macrocyclic esters and lactones utilizing double metal salt catalysts |
US4661285A (en) * | 1986-05-05 | 1987-04-28 | National Distillers And Chemical Corporation | Balsamic fragrance composition and process for preparation |
US4709058A (en) * | 1986-09-19 | 1987-11-24 | National Distillers And Chemical Corporation | Process for the production of macrocyclic esters by the depolymerization of polyesters |
DE19515888A1 (de) * | 1995-04-29 | 1996-10-31 | Huels Chemische Werke Ag | Verfahren zur kontinuierlichen Herstellung von macrocyclischen Verbindungen |
-
1997
- 1997-09-25 DE DE19742307A patent/DE19742307A1/de not_active Withdrawn
-
1998
- 1998-09-12 EP EP98117335A patent/EP0905222A3/de not_active Withdrawn
- 1998-09-18 US US09/157,000 patent/US6034052A/en not_active Expired - Fee Related
- 1998-09-22 BR BR9803591-6A patent/BR9803591A/pt not_active IP Right Cessation
- 1998-09-22 CA CA002248403A patent/CA2248403A1/en not_active Abandoned
- 1998-09-24 JP JP10285877A patent/JPH11209783A/ja active Pending
- 1998-09-25 AU AU87072/98A patent/AU729020B2/en not_active Ceased
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2328704A1 (fr) * | 1975-10-22 | 1977-05-20 | Huels Chemische Werke Ag | Procede de preparation de diesters cycliques de l'acide dodecane-dioique |
US4251448A (en) * | 1979-07-24 | 1981-02-17 | Bayer Aktiengesellschaft | Macrocyclic diesters |
Also Published As
Publication number | Publication date |
---|---|
US6034052A (en) | 2000-03-07 |
CA2248403A1 (en) | 1999-03-25 |
JPH11209783A (ja) | 1999-08-03 |
AU729020B2 (en) | 2001-01-25 |
BR9803591A (pt) | 2000-02-08 |
EP0905222A3 (de) | 2000-04-12 |
AU8707298A (en) | 1999-04-15 |
DE19742307A1 (de) | 1999-04-01 |
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