Cleaning compositions for solid surfaces – auxiliary compositions – With oxygen – halogen – sulfur – or nitrogen containing or... – Ring in the component
Reexamination Certificate
2002-04-02
2003-07-08
Hardee, John (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
With oxygen, halogen, sulfur, or nitrogen containing or...
Ring in the component
C512S021000, C568S336000, C568S442000
Reexamination Certificate
active
06589921
ABSTRACT:
TECHNICAL FIELD
The present invention relates to the perfume industry. More particularly, it is concerned with new cyclic compounds capable of releasing fragrant alcohols.
PRIOR ART
The perfume industry is displaying a particular interest in compounds which are able to prolong a fragrancing effect for a period of time, in particular to mitigate the problems encountered when using volatile perfuming ingredients. Compounds are known which, only under certain conditions of activation such as light, heat, or the presence of enzymes, notably lipases, are capable of releasing a fragrant substance over an extended time period. For example, international patent application WO 95/04809, which belongs to the present applicant, discloses a process for perfuming fabrics washed in the presence of a lipase-containing detergent comprising a compound of formula
The lipase constitutes an activating agent which is necessary to provide the release of a perfuming molecule from the cited compound. These compounds may be used in various applications. The washing of textiles in particular is a field in which scientists are always searching for new means enabling the effect of perfuming substances to be perceived for a period of time after the washing and drying operations. This because many substances which have odours especially suitable for this type of application are known not to be long-lasting on washed items, with the result that their perfuming effect is perceived only briefly. Given the importance of this type of application in the perfume industry, research activity is on-going within this sector, notably with the aim of finding ever more effective solutions to solve the problems mentioned above.
DESCRIPTION OF THE INVENTION
We have now surprisingly discovered the existence of new cyclic compounds that are capable of releasing fragrant alcohols over a long period of time under totally unforeseen and advantageous conditions, that is to say, without any external assistance or activation condition. Thus, contrary to what is known in the prior art, the process of release of a fragrant alcohol by the compounds of the invention does not necessitate the presence of an external catalyst in the reaction medium, for example an enzyme and in particular a lipase. In a textiles-washing application when they are incorporated in a detergent and/or a fabric softener of any kind, these compounds thus enable the characteristic odour of the alcohol to be imparted to the textile and also enable the diffusion effect of this odour to be prolonged so that it develops over a period of time.
The compounds of the invention comply with the following formula,
in which the dotted lines indicate the position of single or double bonds, R
1
represents a radical belonging to a fragrant alcohol of the formula R
1
OH, X represents a nucleophilic group selected from the group consisting of —OH, ═O, —NH
2
or —NHR
3
, R
3
representing a C
1
to C
6
straight-chain or branched hydrocarbon radical, saturated or unsaturated, or an aliphatic or aromatic ring having 5 or 6 carbon atoms, m and n define whole numbers within the range 0 to 2 such that the sum m+n is equal to 1 or 2, p defines a whole number with a value of 0 or 1, each of the symbols R
2
, R
4
, R
5
, R
6
, R
7
, taken independently, represents a hydrogen atom, a C
1
to C
4
straight-chain or branched hydrocarbon radical, saturated or unsaturated, optionally substituted and, taken two by two, they can form aromatic or aliphatic monocyclic, bicyclic or tricyclic substances with the carbon atoms to which they are bound.
Of the compounds of formula (I), menthyl-2-acetylbenzoate has been described by H. G. Rule and J. Smith in J. Chem. Soc., 1926, 553 and by L. Homer and J. Klaus in Liebigs Ann. Chem., 1979, 1232. Similarly, menthyl 2-formylbenzoate has been described by M. V. Bhatt et al. in J. Org. Chem., 1977, 42, 2697, benzyl 2-formylbenzoate has been described by N. Gautier and R. H. Dodd in Synth. Commun., 1998, 28, 3769, octyl 2-formylbenzoate by J. Barry et al., Synthesis, 1985, 40, and finally benzyl 2-acetylbenzoate by A. Kotali et al., Org. Prep. Proced. Int., 1996, 28, 622. However, these documents of the prior art contain no mention, description or suggestion of any use of these compounds in perfumery, in particular as precursors susceptible of releasing fragrant alcohols.
The compounds of the invention are capable of releasing a fragrant alcohol of the formula R
1
OH on hydrolysis of their ester bond. Fragrant alcohol here means an alcohol of current use in perfumery, that is to say, one which is useable as a perfuming ingredient for the preparation of perfumes or perfumed articles. The criteria to be met as a useable perfuming ingredient are known to the person skilled in the art and include, notably, a certain originality of the fragrance, stability, or even a favourable cost/effectiveness ratio. Although it is obviously impossible to provide an exhaustive list of known alcohols of the formula R
1
OH which may be used according to the invention, we mention by way of example anisyl alcohol, fenchyl alcohol, cinnamic alcohol, 9decen-1-ol, phenethylol, citronellol (3,7-dimethyl-6-octen-1-ol), 3-methyl-5-phenyl-1-pentanol (source: Firmenich S. A., Geneva, Switzerland), Mayol® (7p-menthan-1-ol; source: Firmenich S. A., Geneva, Switzerland), dihydromyrcenol (2,6-dimethyl-oct-7-ene-2-ol), alpha-ionol, tetrahydro-ionol, geraniol [(E)-3,7-dimethyl-2,6-octadien-1-ol], nerol (Z)-3,7-dimethyl-2-6-octadien-1-ol, (Z)-3-hexen-1-ol, 1-hexanol, 2-hexanol, 3,3,5-trimethylhexanol, 3,4,5,6,6-pentamethyl-heptan-2-ol, 5-ethyl-2-nonanol, (Z)-6-nonenol, 6,8-dimethyl-2-nonanol, 2,6-nonadien-1-ol, borneol, 1-octen-3-ol, 4-cyclohexyl-2-methyl-2-butanol (source: Firmenich S. A., 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, cyclomethyl-citronellol, decanol, dihydroeugenol, 8-p-methanol, 3,7-dimethyl-1-octanol, 2,6-dimethyl-2-heptanol, dodecanol, octanol, undecanol, 4-methyl-3-decen-1-ol, eugenol, Florol® (tetrahydro-2-isobutyl-4-methyl-4 (2H)-pyranol; source: Firmenich S. A., Geneva, Switzerland), 2-phenoxy-ethanol, isoeugenol, linalol, Tarragol® (2-methoxy-4-propyl-1-cyclohexanol; source: Firmenich S. A., Geneva, Switzerland), vanillin, ethyl-vanillin, anethol, famesol, 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, tetrahydromugol, 3,7-dimethyl-3-octanol, Polysantol® (E)-3,3-dimethyl-5-(2′,2′,3′-trimethyl-3′-cyclopenten-1-yl)-4-penten-2-ol; source: Firmenich S. A., 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-trimethylcyclopent-3-enyl)pent-4-en-2-ol, 2-ethyl-4-(2,2,3-trimethylcyclopent-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-tetrahydropyrane, 2-cyclohexyl propanol, 2-(1,1-dimethyl-ethyl)-4-methyl-cyclohexanol, 1-(2-tert-butyl-cyclo hexyloxy)-2-butanol, 1-(4-isopropyl-cyclohexyl)-ethanol, Limbanol® [1-(2,2,3,6-tetramethyl-cyclohex-1-yl)-3-hexanol; source: Firmenich S. A., Geneva, Switzerland), 1-heptanol, 1-nonanol and 10-undecen-1-ol. It goes without saying that this list is not complete, any alcohol capable of imparting an odour to a product to be perfumed being comprised in the alcohols of formula R
1
OH related to the invention.
The characteristic feature of the invention resides in the fact that the hydrolysis which induces the release of alcohol is facilitated by an auxiliary effect of the ester bond's neighbouring nucleophilic group X. This effect provides a totally unexpected advantage, that is, it permits cleavage of the ester bond by hydrolysis
Billard De Saint-Laumer Jean-Yves
Gräther Otto
Herrmann Andreas
Firmenich SA
Hardee John
LandOfFree
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