EP0908173A2 - Utilisation en parfumerie du 1-méthoxy-2-méthyl-3-phénylpropane, du 1-(2-méthoxypropyl)-4-méthylbenzène et du 3-méthoxy-2,2,3-triméthyl-1-phénylbutane - Google Patents
Utilisation en parfumerie du 1-méthoxy-2-méthyl-3-phénylpropane, du 1-(2-méthoxypropyl)-4-méthylbenzène et du 3-méthoxy-2,2,3-triméthyl-1-phénylbutane Download PDFInfo
- Publication number
- EP0908173A2 EP0908173A2 EP98118176A EP98118176A EP0908173A2 EP 0908173 A2 EP0908173 A2 EP 0908173A2 EP 98118176 A EP98118176 A EP 98118176A EP 98118176 A EP98118176 A EP 98118176A EP 0908173 A2 EP0908173 A2 EP 0908173A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- methoxy
- methyl
- methylbenzene
- methoxypropyl
- trimethyl
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/395—Bleaching agents
- C11D3/3956—Liquid compositions
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
Definitions
- the present invention relates to the field of perfumery. It relates to, more particularly, the use of 1-methoxy-2-methyl-3-phenylpropane, 1- (2-methoxypropyl) -4-methylbenzene and 3-methoxy-2,2,3-trimethyl-1-phenylbutane in as a fragrance ingredient.
- the preferred compound of the present invention is 1-methoxy-2-methyl-3-phenylpropane. Its smell has a dew-rose note which is very natural. In addition, there is a very nice side of exotic fruit type which evokes the smell of lychee. The smell of this ether is free from the earthy-humic note, mushroom which is found in the known compounds cited above and which is a sub-note little appreciated in the type of applications in functional perfumery to which these compounds are destined. In comparison to the ethers cited which are known as that stable ingredients in bleach, 1-methoxy-2-methyl-3-phenylpropane is by far the most flowery, the most rosy, evoking the smell of citronellol and geraniol.
- 1-methoxy-2-methyl-3-phenylpropane is a compound known from the prior art. It has been described in Ind. J. Chem. 27B , 314 (1988) without, however, a synthesis for this molecule having been reported. Furthermore, this reference nowhere mentions the use of this molecule as a perfuming ingredient.
- the invention also relates to two other new compounds which are also suitable for use in bleach.
- One of these compounds is 1- (2-methoxypropyl) -4-methylbenzene which also has a green note which is accompanied by a strong flowery side. We no longer find the fruity note exotic, but the compound smells of anise and ethyl cinnamate which are they also have new notes that are much appreciated in this kind of application.
- the other compound is 3-methoxy-2,2,3-trimethyl-1-phenylbutane, of which the smell can be described as floral and fruity.
- the floral note is of the type floral-animal with phenolic connotations, while the floral note is of the type citrus, typical of grapefruit, intense and very appreciated.
- the two compounds according to the present are particularly suitable for use in bleach and, more generally, for use in aggressive media and / or at pH Student.
- detergents containing agents and laundry activators such as tetraacetylethylenediamine (TAED), agents peroxygen bleaching agents and, in the case of bleach, hypochlorite, but also media containing reducing agents such as products for perms.
- TAED tetraacetylethylenediamine
- agents peroxygen bleaching agents and, in the case of bleach, hypochlorite, but also media containing reducing agents such as products for perms.
- TAED tetraacetylethylenediamine
- media containing reducing agents such as products for perms.
- they are also suitable for other uses in functional perfumery, and cite, as such, applications in liquid or solid detergents intended for treatment of textiles, fabric softeners, or detergent compositions or cleaning products intended for cleaning dishes or various surfaces.
- the use of the compounds according to the invention is not limited to the products mentioned above, they also lend themselves to all other uses common in perfumery, namely the perfuming of soaps and shower gels, products hygiene or hair treatment, as well as ambient deodorants or cosmetic preparations, and even for use in fine perfumery, namely in perfumes and eau de toilette.
- the compounds according to the invention can be used alone or in admixture with other fragrance ingredients, solvents or adjuvants commonly used in perfumery.
- fragrance ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpene hydrocarbons, heterocyclic nitrogen or sulfur compounds, as well as original essential oils natural or synthetic. Many of these ingredients are also listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or more recent versions, or in other works of a similar nature.
- the proportions in which the compounds according to the invention can be incorporated in the aforementioned miscellaneous products vary in a range of values extent. These values are dependent on the nature of the article or product that we want perfume and the desired olfactory effect, as well as the nature of the co-ingredients in a given composition when the compound of the invention is used in mixture with perfume co-ingredients, solvents or adjuvants commonly used in the art.
- the compounds according to the present invention can be synthesized as described below.
- methylcinnamic aldehyde is used which, in the first stage of the synthesis, is hydrogenated in 1- hydroxy-2-methyl-3-phenylpropane using an appropriate catalyst, which may be Raney nickel.
- the product obtained is then etherified using a common etherification agent, such as for example the MH / CH 3 X system in which X is a halogen and M is an alkali metal, to obtain the desired product.
- Ylang type perfume composition for use in a detergent
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Abstract
Description
On a obtenu 19,3 g d'une huile incolore représentant un rendement théorique de 99%.
Odeur : balsamique, chaud, cinnamique.
On a obtenu 265,4 g d'une huile incolore représentant un rendement théorique de 96%.
Après une heure, on a ajouté 270 g d'iodure de méthyle en solution dans 200 ml de THF et la réaction a encore été laissée une heure à température ambiante. On a hydrolysé alors avec une solution 4M d'acide chlorhydrique. Le produit a ensuite été extrait à l'éther et la phase organique a été lavée jusqu'à neutralité.
Après séchage, on a distillé le produit brut (environ 90°C à 14x102 Pa), pour obtenir 173 g (83%) de produit pur.
Les articles ainsi stockés ont ensuite été évalués pour la qualité de leur odeur par des experts parfumeurs.
La valeur de la qualité olfactive résultante est donnée dans le tableau suivant par les lettres A à E ayant les significations
Produit | Températures | ||
3°C | 22°C | 40°C | |
1-méthoxy-2-méthyl-3-phénylpropane | A8 | A7 | B6 |
1-(2-méthoxypropyl)-4-méthylbenzène | A8 | A6 | B5 |
Ingrédients | Parties en poids |
Acétate de linalyle | 20 |
Acétate de verdyle | 80 |
Benzoate de méthyle | 20 |
Cetalox® à 10% | 10 |
Citronellol | 120 |
Dihydromyrcenol | 170 |
Eugénol | 20 |
Géraniol | 200 |
Habanolide® | 200 |
Indol à 10% | 20 |
Iralia® | 100 |
Isobutyrate de phénoxyéthyle | 20 |
Lorysia® | 200 |
Mayol® | 30 |
Méthyl-para-crésol | 10 |
Phénylhexanol | 230 |
4-tert-Butyl-1-cyclohexanol | 50 |
Total | |
Ingrédients | Parties en poids |
Camphre | 150 |
Dodécanitrile | 80 |
Dihydroterpinéol | 70 |
Diphényloxyde | 600 |
Eucalyptol | 450 |
3,7-Diméthyl-3-octanol | 750 |
Total | |
Claims (7)
- Utilisation en tant qu'ingrédient parfumant du 1-méthoxy-2-méthyl-3-phénylpropane, du 1-(2-méthoxypropyl)-4-méthylbenzène ou du 3-méthoxy-2,2,3-triméthyl-1-phénylbutane.
- Composition parfumante ou article parfumé contenant à titre d'ingrédient parfumant le 1-méthoxy-2-méthyl-3-phénylpropane, le 1-(2-méthoxypropyl)-4-méthylbenzène et/ou le 3-méthoxy-2,2,3-triméthyl-1-phénylbutane.
- Article parfumé selon la revendication 2, sous forme d'un parfum ou d'une eau de toilette, d'un savon, d'un gel de douche ou bain, d'un shampoing ou autre produit d'hygiène capillaire, d'une préparation cosmétique, d'un déodorant corporel ou d'air ambiant, d'un détergent ou d'un adoucissant textile, ou d'un produit d'entretien.
- Détergent ou produit chloré contenant à titre d'ingrédient parfumant le 1-méthoxy-2-méthyl-3-phénylpropane, le 1-(2-méthoxypropyl)-4-méthylbenzène et/ou le 3-méthoxy-2,2,3-triméthyl-1-phénylbutane.
- Article selon la revendication 3 ou 4, caractérisé en ce que le détergent est un détergent à milieu agressif et/ou à pH élevé, en particulier l'eau de Javel.
- 1-(2-Méthoxypropyl)-4-méthylbenzène.
- 3-Méthoxy-2,2,3-triméthyl-1-phénylbutane.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH235597 | 1997-10-08 | ||
CH2355/97 | 1997-10-08 | ||
CH235597 | 1997-10-08 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0908173A2 true EP0908173A2 (fr) | 1999-04-14 |
EP0908173A3 EP0908173A3 (fr) | 2000-04-19 |
EP0908173B1 EP0908173B1 (fr) | 2004-02-18 |
Family
ID=4231858
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98118176A Expired - Lifetime EP0908173B1 (fr) | 1997-10-08 | 1998-09-25 | Utilisation en parfumerie du 1-méthoxy-2-méthyl-3-phénylpropane, du 1-(2-méthoxypropyl)-4-méthylbenzène et du 3-méthoxy-2,2,3-triméthyl-1-phénylbutane |
Country Status (5)
Country | Link |
---|---|
US (1) | US5939368A (fr) |
EP (1) | EP0908173B1 (fr) |
JP (1) | JP3697086B2 (fr) |
DE (1) | DE69821700T2 (fr) |
ES (1) | ES2216225T3 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108498411A (zh) * | 2018-06-28 | 2018-09-07 | 厦门柔丝丽生物科技有限公司 | 一种花瓣沐浴露及其制备方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10325862A1 (de) * | 2003-06-06 | 2004-12-23 | Bayerische Motoren Werke Ag | Festoxid-Brennstoffzelle mit einem metallischen Trägersubstrat |
US7663342B2 (en) * | 2007-01-26 | 2010-02-16 | Solarbridge Technologies, Inc. | Apparatus, system, and method for controlling multiple power supplies |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2976327A (en) * | 1959-06-09 | 1961-03-21 | Givaudan Corp | Alpha-methylhydrocinnamic aldehyde dimethyl acetal |
EP0622451A1 (fr) * | 1993-04-26 | 1994-11-02 | The Procter & Gamble Company | Compostions parfumées de blanchiment à l'hypochlorite |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4371715A (en) * | 1981-02-19 | 1983-02-01 | International Flavors & Fragrances Inc. | Process for preparing cyclohexyl phenethylether derivatives |
SU1296559A1 (ru) * | 1985-04-02 | 1987-03-15 | Институт Органической Химии Ан Армсср | Способ получени 3-метокси-1-фенил-1-пропена |
US5248434A (en) * | 1992-04-20 | 1993-09-28 | The Proctor & Gamble Company | Liquid or gel bleaching composition containing amidoperoxyacid bleach and perfume |
JP3197371B2 (ja) * | 1992-11-04 | 2001-08-13 | 稲畑香料株式会社 | 芳香を有する過酢酸系殺菌剤組成物及び漂白剤組成物 |
-
1998
- 1998-09-22 US US09/157,953 patent/US5939368A/en not_active Expired - Lifetime
- 1998-09-25 DE DE69821700T patent/DE69821700T2/de not_active Expired - Lifetime
- 1998-09-25 EP EP98118176A patent/EP0908173B1/fr not_active Expired - Lifetime
- 1998-09-25 ES ES98118176T patent/ES2216225T3/es not_active Expired - Lifetime
- 1998-10-05 JP JP28257198A patent/JP3697086B2/ja not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2976327A (en) * | 1959-06-09 | 1961-03-21 | Givaudan Corp | Alpha-methylhydrocinnamic aldehyde dimethyl acetal |
EP0622451A1 (fr) * | 1993-04-26 | 1994-11-02 | The Procter & Gamble Company | Compostions parfumées de blanchiment à l'hypochlorite |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Week 198740 Derwent Publications Ltd., London, GB; AN 1987-283650 XP002131502 & SU 1 296 559 A (AS. ARMN. ORG. CHEM.), 15 mars 1987 (1987-03-15) * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108498411A (zh) * | 2018-06-28 | 2018-09-07 | 厦门柔丝丽生物科技有限公司 | 一种花瓣沐浴露及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JPH11199890A (ja) | 1999-07-27 |
DE69821700T2 (de) | 2004-12-02 |
EP0908173B1 (fr) | 2004-02-18 |
US5939368A (en) | 1999-08-17 |
ES2216225T3 (es) | 2004-10-16 |
DE69821700D1 (de) | 2004-03-25 |
JP3697086B2 (ja) | 2005-09-21 |
EP0908173A3 (fr) | 2000-04-19 |
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