Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
2002-03-25
2004-01-13
Hardee, John R (Department: 1751)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C510S102000, C560S008000
Reexamination Certificate
active
06677297
ABSTRACT:
TECHNICAL FIELD
The present invention relates to the field of perfumery. More particularly, it concerns new esters capable of liberating an odoriferous alcohol and comprising, in proximity, a carbamoyl function facilitating the liberation of the said odoriferous alcohol.
PRIOR ART
The perfumery industry has a particular interest in compounds which are capable of prolonging an odoriferous effect over a certain period of time, in particular in order to overcome the problems encountered when using perfuming ingredients which are too volatile. U.S. Pat. No. 5,649,979 in particular discloses compounds which, under certain activation conditions such as light, heat or the presence of enzymes, in particular lipases, are capable of liberating an odoriferous molecule over an extended period of time. These compounds can have various applications. The washing of textiles is a particular field in which there is a constant quest to enable the effect of perfuming substances to be experienced for a certain period after washing and drying. Many substances having fragrances which are particularly suitable for this type of application are, in fact, known to lack tenacity on laundry, or do not remain on the laundry when rinsed, with the result that their perfuming effect is experienced only briefly and not very intensely. Given the importance of this type of application in the perfuming industry, research in this field has been sustained, in particular with the aim of finding new, even more effective solutions to the aforementioned problems.
DESCRIPTION OF THE INVENTION
Surprisingly, we have discovered the existence of new esters comprising a non-substituted or mono-substituted carbamoyl function capable of liberating, in a controlled and effective manner, an odoriferous alcohol without the aid of an activator as described in the prior art. Furthermore, these compounds have, quite unexpectedly, excellent staying-power or tenacity, especially on laundry, making them very suitable precursors in particular for applications associated with functional perfumery. Odoriferous molecules present as such in products such as washing powders or detergents generally have little staying-power and are consequently often eliminated in the rinsing water during machine washing, for example. Conversely, the compounds according to the invention, owing to their substantivity and the controlled liberation of the odoriferous alcohol, can impart a fragrance and a freshness to laundry which will last beyond the rinsing and drying processes.
The compounds of the present invention have the following formula:
in which the dotted line indicates the location of a single or double bond; R
1
represents a radical derived from an odoriferous alcohol of the formula R
1
OH; R
2
represents a hydrogen atom, a linear or branched, saturated or unsaturated C
1
-C
30
hydrocarbon radical, or an aliphatic or aromatic cyclic compound having 5 or 6 carbon atoms, this radical R
2
possibly comprising heteroatoms of oxygen, sulphur or nitrogen, in particular quaternary ammonium functions; the symbols R
3
, R
4
and R
4
′, considered independently, represent a hydrogen atom, a linear or branched, saturated or unsaturated, if necessary substituted, C
1
to C
20
hydrocarbon radical possibly comprising one or more heteroatoms, or, when considered together with the carbon atoms to which they are bonded, can form aromatic or aliphatic monocyclic, bicyclic or tricyclic compounds, the radicals R
3
, R
4
and R
4
′ possibly comprising functional groups of the ester and carbamoyl type so as to liberate several molecules of odoriferous alcohol R
1
OH per single molecule of precursor. This is the case in particular for the products of pyromellitic anhydride, as indicated hereinbelow.
These compounds are capable of liberating an odoriferous alcohol of the formula R
1
OH during the hydrolysis of the ester bond. Odoriferous alcohol is taken here to mean an alcohol commonly used in perfumery, that is to say suitable as a perfuming ingredient for the preparation of perfumes or perfumed articles. Although it is not possible to provide an exhaustive list of the currently known alcohols of the formula R
1
OH usable according to the invention, the following can be named as examples: anisyc alcohol, cinnamic alcohol, fenchyl alcohol, 9-decen-1-ol, phenethylol, citronellol (3,7-dimethyl-6-octen-1-ol), 3-methyl-5-phenyl-1-pentanol (origin: Firmenich SA, Geneva, Switzerland), Mayol® (7-p-menthan-1-ol; origin: Firmenich SA, Geneva, Switzerland), dihydromyrcenol (2,6-dimethyl-oct-7-en-2-ol), alpha-ionol, tetrahydro-ionol, geraniol, nerol, (Z)-3-hexen-1-ol, 1-hexanol, 2-hexanol, 3,3,5-trimethyl-hexanol, 3,4,5,6,6-pentamethyl-heptan-2-ol, 5-ethyl-2-nonanol, cis-6-nonenol, 6,8-dimethyl-2-nonanol, 2,6-nonadien-1-ol, borneol, 1-octen-3-ol, 4-cyclohexyl-2-methyl-2-butanol (origin: Firmenich SA, Geneva, Switzerland), 6-ethyl-3-methyl-5-octen-1-ol, 3,7-dimethyl-oct-3,6-dienol, 7-methoxy-3,7-dimethyl-octan-2-ol, methyl-4-phenyl-2-butanol, 2-methyl-1-phenyl-2-propanol, 1-phenylethanol, 2-phenylethanol, 2-phenylpropanol, 3-phenylpropanol, 2-methyl-5-phenylpentanol, 2-methyl-4-phenylpentanol, 3-methyl-5-phenylpentanol, cyclomethylcitronellol, decanol, dihydroeugenol, 8-p-menthanol, 3,7-dimethyl-1-octanol, 2,6-dimethyl-2-heptanol, dodecanol, octanol, undecanol, 4-methyl-3-decen-1-ol, eucalyptol, eugenol, Florol® (tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol; origin: Firmenich SA, Geneva, Switzerland), 2-phenoxy-ethanol, isoeugenol, linalol, Tarragol® (2-methoxy-4-propyl-1-cyclohexanol; origin: Firmenich SA, Geneva, Switzerland), vanillin, ethyl-vanillin, anethole, farnesol, cedrenol, menthol, p-menth-8-en-3-ol, 3,3,5-trimethyl-cyclohexanol, 2,4,6-trimethyl-3-cyclohexenyl-methanol, 4-(1-methylethyl) cyclohexyl-methanol, terpineol, tetrahydromuguol, 3,7-dimethyl-3-octanol, Polysantol® [(E)-3,3-dimethyl-5-(2′,2′,3′-trimethyl-3′-cyclopenten-1-yl)-4-penten-2-ol; origin: Firmenich SA, Geneva, Switzerland], 2,2,6-trimethyl-alpha-propyl-cyclohexane propanol, 5-(2,2,3-trimethyl-3-cyclopentyl)-3-methylpentan-2-ol, 3-methyl-5-(2,2,3-trimethylcyclopentyl-3-enyl)pent-4-en-2-ol, 2-ethyl-4(2,2,3-trimethylcyclo-pentyl-3-enyl)but-2-en-1-ol, 4-(5,5,6-trimethylbicyclo[2.2.1]hept-2-yl)-cyclohexanol, 2-(2-methyl-propyl)-4-hydroxy-4-methyl-tetrahydropyran, 2-cyclohexyl-propanol, 2-(1,1-dimethylethyl)-4-methyl-cyclohexanol, 1-(2-tert-butyl-cyclo-hexyloxy)-2-butanol, 1-(4-isopropyl-cyclohexyl)-ethanol and 1-(2,2,3,6-tetramethyl-cyclohex-1-yl)-3-hexanol (origin: Firmenich SA, Geneva, Switzerland).
The special feature of the invention resides in the fact that hydrolysis, which causes liberation of the alcohol, is assisted by the nucleophilic group adjacent to the ester function, the CONH—R
2
group. This assistance has a completely unexpected advantage, i.e. it permits the cleavage of the ester bond by hydrolysis in simple alkaline conditions, as shown by the following scheme:
Such conditions are the normal conditions for washing textiles, for example, during the course of which a change in pH takes place. The pH changes from a value corresponding to an acid environment to values corresponding to a neutral or even basic environment during the course of the washing cycle, thus allowing the compounds according to the invention to hydrolyse.
Furthermore, the reaction is catalysed naturally in the presence of heat. This is the case e.g. when laundry is dried, in particular in an electric dryer, or ironed, especially steam ironed. The hydrolysis reaction leads to the formation of an odoriferous molecule R
1
OH, in which R
1
, has the meaning indicated hereinabove, and a residue of the initial precursor, an imide, this residue generally being odourless.
The reaction does not require any other external agent such as the presence of a lipase, as described in the prior art.
The compounds according to the invention have thus proved to be advantageous precursors of odoriferous alcohols. The hydrolysis reaction of the ester bond in the most simple conditions
Firmenich SA
Hardee John R
Winston & Strawn LLP
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