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 dewy rose leaf 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 being 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 also new notes very 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 and, in the case of bleach, hypochlorite, but also media containing reducing agents such as products for perms.
• TAED tetraacetylethylenediamine
• agents peroxygen bleaching 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 or bath gels, products hygiene or hair treatment, shampoo as well as ambient air fresheners 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 extended. 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.
• 3-methoxy-2,2,3-trimethyl-1-phenylbutane (see line (3) of the diagram below) is prepared from 3,3-dimethyl-4-phenyl-2-butanone that it is reacted with the magnesium of a methyl halide, for example bromide or iodide, in order to obtain the 2,3,3-trimethyl-4-phenyl-2-butanol alcohol. Said alcohol is then etherified to the desired final product as described above for the other compounds of the invention.
• a methyl halide for example bromide or iodide
• the magnesium of bromotoluene was prepared from 400 g of bromotoluene and 63 g of magnesium. To this magnesium was added at room temperature 150 g of propylene oxide in 20 minutes. After one hour at this temperature, it was hydrolyzed with one liter of a 4M hydrochloric acid solution. The product was extracted with ether, and this organic phase was washed several times until neutral, then dried over MgSO 4 . This crude product was distilled on a column to provide 320 g of desired alcohol (91%).
• a solution of methyl iodide magnesium was prepared from 21.7 g of methyl iodide, 3.4 g of magnesium and 80 ml of diethyl ether in a three-necked flask equipped with a condenser, a thermometer and '' a bulb to introduce and under a nitrogen atmosphere.
• a solution of 3,3-dimethyl-4-phenyl-2-butanone (prepared according to the recipe described in application DE 3210725) was then added in 70 ml of diethyl ether, leaving to react under reflux. The reaction mixture was stirred at room temperature overnight, then poured onto ice, washed to neutrality with a saturated NH 4 Cl solution and dried over MgSO 4 .
• This compound was prepared in a manner analogous to that described in 1b) from the alcohol prepared previously (12 g, 0.048 mole), 10.4 ml of a suspension of KH at 20% in oil ( 0.06 mole) and 8.74 g (0.062 mole) of methyl iodide, and 70 ml of THF. 10.1 g of a product having a boiling point of 56 ° / 1.2 ⁇ 10 1 Pa were thus obtained. A product with a purity of 99% can be obtained by subjecting this distillation product to chromatography on an SiO 2 column using a cyclohexane / diethyl ether mixture as eluent.
• Ylang type perfume composition for use in a detergent

Applications Claiming Priority (3)

Publications (3)

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• 1998
  • 1998-09-22 US US09/157,953 patent/US5939368A/en 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
  • 1998-09-25 DE DE69821700T patent/DE69821700T2/de not_active Expired - Lifetime
  • 1998-10-05 JP JP28257198A patent/JP3697086B2/ja not_active Expired - Lifetime

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