Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
1998-04-24
2002-10-01
Warden, Jill (Department: 1743)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C512S020000, C512S025000, C560S055000, C560S064000, C560S066000, C560S103000, C424S069000, C424S076400, C510S102000, C510S107000
Reexamination Certificate
active
06458757
ABSTRACT:
The present invention relates to a process for the production of perfuming compositions, to perfumed products, and to products so obtained.
In particular, the present invention envisages their use in the perfumery field. The compounds exhibit very interesting olfactory properties and can be used, inter alia, to prepare perfuming compositions and perfumed products.
The perfumery industry is constantly seeking products which by their originality, volume and the strength of their fragrance can endow compositions containing them with a unique character.
We have now discovered that alkylsalicylic acid esters as defined below, in particular methylsalicylic acid esters, exhibit novel olfactory properties.
It should be noted that it is impossible for the skilled person to predict whether a given chemical compound will or will not have an interesting scent from the olfactory viewpoint which could be used in the perfumery field.
More specifically, the present invention concerns a process for the production of perfuming compositions, perfumed products and substances for perfumery characterized in that an effective quantity of an alkylsalicylic acid ester is added to the usual constituents of these compositions, substances and finished products.
The present invention also concerns perfuming compositions, perfumed substances and products characterized in that they comprise, as an active ingredient having an influence on the scent, an effective quantity of an alkylsalicylic acid ester.
The invention thus resides in a novel use of esters of an alkylsalicylic acid as a perfuming ingredient.
The invention also relates to certain alkylsalicylic acid esters as novel products.
The perfuming ingredient of the invention is an alkylsalicylic acid ester. More particularly, it has the following general formula (I):
in which formula (I):
n is a number equal to 1 or 2.
R
1
represents a hydrocarbon radical which may or may not be substituted, containing 1 to 40 carbon atoms, more particularly a linear or branched, saturated or unsaturated, aliphatic, acyclic radical, or a saturated or unsaturated, monocyclic or polycyclic, carbocyclic or heterocyclic radical;
R
2
represents an aliphatic radical, preferably saturated, preferably less than 4.
More particularly, the alkylsalicylic acid esters have formula (I) in which the different radicals R
1
and R
2
have the following meaning.
The number of carbon atoms in R
1
is generally between 1 and 40 carbon atoms, preferably between 1 and 12 carbon atoms.
Radical R
1
can be a monovalent radical which may or may not be substituted, which may be a linear or branched, saturated or unsaturated, aliphatic acyclic radical; or a saturated or unsaturated, monocyclic or polycyclic, carbocyclic or heterocyclic radical.
Radical R
1
is a linear or branched, saturated or unsaturated, aliphatic acyclic radical.
More precisely, R
1
is a linear or branched alkyl, alkenyl or alkadienyl radical preferably containing 1 to 40 carbon atoms.
The hydrocarbon chain can optionally be interrupted by a heteroatom (for example oxygen or sulphur) or by one of the following groups: —CO—, —COO—, and/or can carry one of the following substituents: —OH, —COOR
3
, —, —CF
3
: in these formulae, R
3
preferably represents hydrogen or a linear or branched alkyl radical containing 1 to 4 carbon atoms, more particularly a methyl or ethyl radical.
R
1
can represent a carbocyclic monocyclic radical. The number of carbon atoms in the cycle can vary from 3 to 8 carbon atoms, but is preferably 5 or 6 carbon atoms.
The carbocycle can be saturated or can contain 1 or 2 unsaturated bonds in the cycle, preferably 1 or 2 double bonds.
Examples of carbocycles area cycloalkoyl or cycloalkenyl radical containing 3 to 8 carbon atoms, preferably a cyclohexyl, cyclohexen-yl or cyclohepten-yl radical.
When R
1
represents a saturated or unsaturated carbocyclic monocyclic radical, it is possible for one or more carbon atoms of the cycle to be replaced by one or more heteroatoms, preferably oxygen, nitrogen or sulphur or by a functional group, preferably a carbonyl or ester group, resulting in a heterocyclic monocyclic compound. The number of atoms in the cycle can vary from 3 to 8 atoms but is preferably 5 or 6 atoms.
Radical R
1
can also be carbocyclic and polycyclic, preferably bicyclic which means that at least two cycles have two carbon atoms in common. For polycyclic radicals, the number of carbon atoms in each cycle is between 3 and 6: the total number of carbon atoms is preferably 7.
Examples of currently encountered bicyclic structures are given below:
Radical R
1
can also be heterocyclic and polycyclic, preferably bicyclic, meaning that at least two cycles have two atoms in common. In this case, the number of atoms in each cycle is between 3 and 6, more preferably 5 or 6.
Radical R
1
can represent a linear or branched, saturated or unsaturated aliphatic radical carrying a cyclic substituent. Examples of cyclic substituents are cycloaliphatic, aromatic or heterocyclic substituents, in particular cycloaliphatic compounds containing 6 carbon atoms in the cycle, or benzene rings. More particular examples are arylalkyl radicals containing 6 to 12 carbon atoms, preferably the benzyl radical.
It should be noted that if radical R
1
contains a cycle, it is possible for the cycle to carry a substituent of any type. The substituents usually carried by the cycle are one or more alkyl or alkoxy radicals preferably containing 1 to 4 carbon atoms, preferably three methyl radicals, a methylene radical (corresponding to an exocyclic bond), an alkenyl radical, preferably an isopropen-yl radical, or a halogen atom, preferably chlorine or bromine.
More preferably, the alkylsalicylic acid esters have the following general formula (Ia):
in which formula (Ia):
n is a number equal to 1 or 2;
R
1
represents a linear or branched alkyl radical containing 1 to 12 carbon atoms, preferably 1 to 8: or a cycloalkyl radical preferably containing 6 carbon atoms, or an aralkyl radical containing 6 to 12 carbon atoms, preferably 7 or 8 carbon atoms;
R
2
represents a linear or branched alkyl radical containing 1 to 4 carbon atoms, preferably 1 or 2.
Of compounds with formula (I), those in which radical R
1
contains more than two carbon atoms are novel products and are claimed as such.
Preferred compounds are those with formula (Ia) in which R
1
represents an alkyl radical such as methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, n-hexyl, 2-ethylhexyl; a cyclohexyl radical; or a benzyl radical or a &bgr;-phenylethyl radical, and R
2
represents a methyl or ethyl radical.
Specific examples of alkylsalicylic acid esters with formula (I) are, among others:
methyl 2-hydroxy-3-methyl-benzoate;
ethyl 2-hydroxy-3-methyl-benzoate;
isopropyl 2-hydroxy-3-methyl-benzoate;
n-propyl 2-hydroxy-3-methyl-benzoate;
n-butyl 2-hydroxy-3-methyl-benzoate;
isobutyl 2-hydroxy-3-methyl-benzoate;
amyl 2-hydroxy-3-methyl-benzoate;
isoamyl 2-hydroxy-3-methyl-benzoate;
n-hexyl 2-hydroxy-3-methyl-benzoate;
2-ethylhexyl 2-hydroxy -3-methyl-benzoate;
cyclohexyl 2-hydroxy-3-methyl-benzoate;
benzyl 2-hydroxy-3-methyl-benzoate;
&bgr;-phenylethyl 2-hydroxy-3-methyl-benzoate;
methyl 2-hydroxy-4-methyl-benzoate;
ethyl 2-hydroxy-4-methyl-benzoate;
isopropyl 2-hydroxy-4-methyl-benzoate;
n-propyl 2-hydroxy-4-methyl-benzoate;
n-butyl 2-hydroxy-4-methyl-benzoate;
isobutyl 2-hydroxy-4-methyl-benzoate;
amyl 2-hydroxy-4-methyl-benzoate;
isoamyl 2-hydroxy-4-methyl-benzoate;
n-hexyl 2-hydroxy-4-methyl-benzoate;
2-ethylhexyl 2-hydroxy-4-methyl-benzoate;
cyclohexyl 2-hydroxy-4-methyl-benzoate;
benzyl 2-hydroxy-4-methyl-benzoate;
&bgr;-phenylethyl 2-hydroxy-4-methyl-benzoate;
methyl 2-hydroxy-5-methyl-benzoate;
ethyl 2-hydroxy-5-methyl-benzoate;
isopropyl 2-hydroxy-5-methyl-benzoate;
n-propyl 2-hydroxy-5-methyl-benzoate;
n-butyl 2-hydroxy-5-methyl-benzoate;
isobutyl 2-hydroxy-5-methyl-benzoate;
amyl 2-hydroxy-5-methyl-benzoate;
isoamyl 2-hydroxy-5-methyl-benzoate;
n-hexyl 2-hydroxy-5-methyl-benzoate;
2-ethylhexyl 2-hydroxy-5-methyl-benzo
Chimie Rhodia
Cole Monique T.
Warden Jill
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